US 2012/0232068 A1Published application

Quinazolines as potassium ion channel inhibitors

AssigneeBriston-Myers Squibb Company

InventorsJames A. Johnson, John Lloyd, Heather Finlay, Ji Jiang, James Neels, Naveen Kumar Dhondi, Prashantha Gunaga, Abhisek Banerjee

Life of this patent

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Abstract

A compound of formula (I) wherein A, X, Y, Z, R1 and R24 are described herein. The compounds are useful as inhibitors of potassium channel function and in the treatment and prevention of arrhythmia, IKur associated disorders, and other disorders mediated by ion channel function.

Claims40

Dependent claims

A compound of formula I

or an enantiomer, diastereomer, tautomer, or salt thereof wherein:
X is H, —OH, F, Cl, Br, I, C1-10 alkyl, C1-10 alkoxy, haloC1-10 alkyl, C2-12 alkenyl, C2-12 alkynyl, C3-10 cycloalkyl, a 4- to 12-membered heteroaryl, 4- to 12-membered heterocyclyl, —CN, —NO2, —NR11SO2R12, —SO2NR11R12, —CONR11R12, —NR11CONR11R12, —NCOR11, —NR11SO2NR11R12, —OCONR11R12, —CO2R11 or —NR11R12;
Y is H, F, Cl, Br, I, C1-10 alkyl, C1-10 alkoxy, haloC1-10 alkyl, C2-12 alkenyl, C2-12 alkynyl, C3-10 cycloalkyl, a 4- to 12-membered heteroaryl, 4- to 12-membered heterocyclyl, —CN, —NO2, —SO2NR11R12, —CONR11R12, —NR11CONR11R12, —NCOR11, —NR11SO2NR11R12, —OCONR11R12, —CO2R11 or —NR11R12;
Z is H, Cl, Br, I, C1-10 alkyl, C1-10 alkoxy, haloC1-10 alkyl, C2-12 alkenyl, C2-12 alkynyl, C3-10 cycloalkyl, a 6- to 12-membered heteroaryl, 4- to 12-membered heterocyclyl, —NO2, —NR11SO2R12, —SO2NR11R12, —NR11CONR11R12, —NCOR11, —NR11SO2NR11R12, —OCONR11R12, —CO2R11 or —NR11R12;
A is —(CH2)m—R2, —CH(R25)(R26), —CH(R26)—CO2—R2a or —(CH2)n-1—NR25—CO2—R24;
m is 0 to 4;
n is 1 to 4;
n-1 is 2 to 4;
R1 is —OH, F, Cl, Br, I, C1-10 alkyl, haloC1-10 alkyl, C2-12 alkenyl, C3-10 cycloalkyl, —CN, —(CH2)m—SO2NR11R12, —(CH2)m—CO2R11 or —(CH2)n—NR11SO2R12, wherein the alkenyl and cycloalkyl may be optionally substituted with one or more RD's;
or
R1 is selected from the group consisting of:
Or
R1 is
R2 is C1-10 alkyl, cyclopropyl optionally substituted with one or more R13′5;
C4-10 cycloalkyl optionally substituted with one or more R13bb's;
C3-10 cycloalkenyl optionally substituted with one or more R13b's;
or —NR14R14;
provided that R2 is not —NR14R14 when m is 0, 1 or 3;
or
R2 is
or
R2 is selected from the group consisting of:
R2a is C1-10 alkyl, C3-10 cycloalkyl, C6-10 aryl, —NR14R14, a 4- to 12-membered heteroaryl or 4- to 12-membered heterocyclyl, any of which is optionally substituted with one or more R13's and the heteroaryl and heterocyclyl consist of carbon atoms and 1, 2, 3, or 4 heteroatoms independently selected from the group consisting of N, S, or O;
R11 and R12, at each occurrence, are independently selected from H, C1-10 alkyl, haloC1-10 alkyl, C3-10 cycloalkyl, C6-10aryl, a 4- to 12-membered heteroaryl and a 4- to 12-membered heterocyclyl, wherein the alkyl, cycloalkyl, aryl, heteroaryl and heterocyclyl may be optionally substituted with one or more R13's and the heteroaryl and heterocyclyl consist of carbon atoms and 1, 2, 3, or 4 heteroatoms independently selected from the group consisting of N, S, or O;
or
R11 and R12 are taken together with the nitrogen to which they are attached to form a 4- to 12-membered heterocyclyl, wherein the heterocyclyl may be optionally substituted with one or more R13's and the heterocyclyl consists of carbon atoms and 1, 2, 3, or 4 heteroatoms independently selected from the group consisting of N, S, or O;
R13, at each occurrence, is independently H, —OH, F, Cl, Br, I, C1-10 alkyl, C1-10 alkoxy, haloC1-10 alkyl, C3-10 cycloalkyl, C2-12 alkenyl, C2-12 alkynyl, C6-10aryl, a 4- to 12-membered heteroaryl, a 4- to 12-membered heterocyclyl, a 4- to 12-membered heteroaryl-C1-10 alkyl, —CN, —NO2, —(CH2)m—SO2R14, —NR14SO2R14, —O, —CONR14R14, —(CH2)m—SO2NR14R14, —(CH2)m—NR14SO2R14, —(CH2)m—NR14SO2NR14R14, —NR14SO2NR14R14, —CO2NR14R14, —NR14CO2NR14R14, —NR14COR14, —SO2NR14COR14, —SO2NR14CONR14R14, —NR14CO2R14, —CO2R14, —NR14R14, —NR14CONR14R14, —C(═NOR14)NR14R14, —CONR14OR14 or —NCOR14, wherein the alkyl, cycloalkyl, alkenyl, alkoxy, aryl, heteroaryl and heterocyclyl may be optionally substituted with one or more R14a's and the heteroaryl and heterocyclyl consist of carbon atoms and 1, 2, 3, or 4 heteroatoms independently selected from the group consisting of N, S, or O;
provided that when R13 is alkyl substituted with one R14a, R14a is not —OH;
R13a, at each occurrence, is independently H, —OH, F, Cl, Br, I, C2-10 alkyl, C1-10 alkoxy, haloC1-10 alkyl, C3-10 cycloalkyl, C2-12 alkenyl, C2-12 alkynyl, C6-10aryl, a 4- to 12-membered heteroaryl, a 4- to 12-membered heterocyclyl, a 4- to 12-membered heteroaryl-C1-10 alkyl, —CN, —NO2, —(CH2)m—SO2R14, —NR14SO2R14, ═O, —CONR14R14, —(CH2)m—NR14SO2R14, —(CH2)m—NR14SO2NR14R14, —NR14SO2NR14R14, —CO2NR14R14, —NR14CO2NR14R14, —NR14COR14, —SO2NR14COR14, —SO2NR14CONR14R14, —NR14CO2R14, —CO2R14, —NR14R14, —NR14CONR14R14, —C(═NOR14)NR14R14, —CONR14OR14 or —NCOR14, wherein the alkyl, cycloalkyl, alkenyl, alkoxy, aryl, heteroaryl and heterocyclyl may be optionally substituted with one or more R14a's and the heteroaryl and heterocyclyl consist of carbon atoms and 1, 2, 3, or 4 heteroatoms independently selected from the group consisting of N, S, or O;
R13aa, at each occurrence, is independently H, —OH, F, Cl, Br, I, C1-10 alkyl, C1-10 alkoxy, haloC1-10 alkyl, C3-10 cycloalkyl, C2-12 alkenyl, C2-12 alkynyl, C6-10aryl, a 4- to 12-membered heteroaryl, a 4- to 12-membered heterocyclyl, a 4- to 12-membered heteroaryl-C1-10 alkyl, —CN, —NO2, —(CH2)m—SO2R14, —NR14SO2R14, —O, —CONR14R14, —(CH2)m—SO2NR14R14, —(CH2)m—NR14SO2R14, —(CH2)m—NR14SO2NR14R14, —NR14SO2NR14R14, —CO2NR14R14, —NR14CO2NR14R14, —NR14COR14, —SO2NR14COR14, —SO2NR14CONR14R14, —NR14CO2R14, —CO2R14, —NR14R14, —NR14CONR14R14, —C(═NOR14)NR14R14, —CONR14OR14 or —NCOR14, wherein the alkyl, cycloalkyl, alkenyl, alkoxy, aryl, heteroaryl and heterocyclyl may be optionally substituted with one or more R14a's and the heteroaryl and heterocyclyl consist of carbon atoms and 1, 2, 3, or 4 heteroatoms independently selected from the group consisting of N, S, or O;
R13a-1, at each occurrence, is independently H, —OH, F, Cl, Br, I, C1-10 alkyl, C1-10 alkoxy, haloC1-10 alkyl, C3-10 cycloalkyl, C2-12 alkenyl, C2-12 alkynyl, C6-10aryl, a 4- to 12-membered heteroaryl, a 4- to 12-membered heterocyclyl, a 4- to 12-membered heteroaryl-C1-10 alkyl, —CN, —NO2, —(CH2)m—SO2R14, —NR14SO2R14, ═O, —CONR14R14, —(CH2)m—SO2NR14R14, —(CH2)m—NR14SO2R14, —(CH2)m—NR14SO2NR14R14, —NR14SO2NR14R14, —CO2NR14R14, —NR14CO2NR14R14, —NR14COR14, —SO2NR14COR14, —SO2NR14CONR14R14, —NR14CO2R14, —CO2R14, —NR14R14, —NR14CONR14R14, —C(═NOR14)NR14R14, —CONR14OR14 or —NCOR14, wherein the alkyl, cycloalkyl, alkenyl, alkoxy, aryl, heteroaryl and heterocyclyl may be optionally substituted with one or more R14a's and the heteroaryl and heterocyclyl consist of carbon atoms and 1, 2, 3, or 4 heteroatoms independently selected from the group consisting of N, S, or O;
R13a-2, at each occurrence, is independently H, —OH, F, Br, I, C1-10 alkyl, C1-10 alkoxy, haloC1-10 alkyl, C3-10 cycloalkyl, C2-12 alkenyl, C2-12 alkynyl, C6-10aryl, a 4- to 12-membered heteroaryl, a 4- to 12-membered heterocyclyl, a 4- to 12-membered heteroaryl-C1-10 alkyl, —CN, —NO2, —(CH2)m—SO2R14, —NR14SO2R14, ═O, —CONR14R14, —(CH2)m—SO2NR14R14, —(CH2)m—NR14SO2R14, —(CH2)m—NR14SO2NR14R14, —NR14SO2NR14R14, —CO2NR14R14, —NR14CO2NR14R14, —NR14COR14, —SO2NR14COR14, —SO2NR14CONR14R14, —NR14CO2R14, —CO2R14, —NR14R14, —NR14CONR14R14, —C(═NOR14)NR14R14, —CONR14OR14 or —NCOR14, wherein the alkyl, cycloalkyl, alkenyl, alkoxy, aryl, heteroaryl and heterocyclyl may be optionally substituted with one or more R14a's and the heteroaryl and heterocyclyl consist of carbon atoms and 1, 2, 3, or 4 heteroatoms independently selected from the group consisting of N, S, or O;
R13a-4, at each occurrence, is independently H, —OH, F, Cl, Br, I, C1-10 alkyl, C1-10 alkoxy, haloC1-10 alkyl, C3-10 cycloalkyl, C2-12 alkenyl, C2-12 alkynyl, C6-10aryl, a 4- to 12-membered heteroaryl, a 4- to 12-membered heterocyclyl, a 4- to 12-membered heteroaryl-C1-10 alkyl, —CN, —NO2, —(CH2)m—SO2R14, —NR14SO2R14, ═O, —CONR14R14, —(CH2)m—SO2NR14R14, —(CH2)m—NR14SO2R14, —(CH2)m—NR14SO2NR14R14, —NR14SO2NR14R14, —CO2NR14R14, —NR14CO2NR14R14, —NR14COR14, —SO2NR14COR14, —SO2NR14CONR14R14, —NR14CO2R14, —CO2R14, —NR14R14, —NR14CONR14R14, —C(═NOR14)NR14R14, —CONR14OR14 or —NCOR14, wherein the alkyl, cycloalkyl, alkenyl, alkoxy, aryl, heteroaryl and heterocyclyl may be optionally substituted with one or more R14a's and the heteroaryl and heterocyclyl consist of carbon atoms and 1, 2, 3, or 4 heteroatoms independently selected from the group consisting of N, S, or O;
R13b, at each occurrence, is independently H, F, Cl, Br, I, C1-10 alkyl, C1-10 alkoxy, haloC1-10 alkyl, C3-10 cycloalkyl, C2-12 alkenyl, C2-12 alkynyl, C6-10aryl, a 4- to 12-membered heteroaryl, a 4- to 12-membered heterocyclyl, a 4- to 12-membered heteroaryl-C1-10 alkyl, —CN, —NO2, —(CH2)m—SO2R14, —NR14SO2R14, ═O, —(CH2)m—SO2NR14R14, —(CH2)m—NR14SO2R14, —(CH2)m—NR14SO2NR14R14, —NR14SO2NR14R14, —CO2NR14R14, —NR14CO2NR14R14, —NR14COR14, —SO2NR14COR14, —SO2NR14CONR14R14, —NR14CO2R14, —CO2R14, —NR14R14, —NR14CONR14R14, —C(═NOR14)NR14R14, —CONR14OR14 or —NCOR14, wherein the alkyl, cycloalkyl, alkenyl, alkoxy, aryl, heteroaryl and heterocyclyl may be optionally substituted with one or more R14a's and the heteroaryl and heterocyclyl consist of carbon atoms and 1, 2, 3, or 4 heteroatoms independently selected from the group consisting of N, S, or O;
R13bb, at each occurrence, is independently H, F, Cl, Br, I, C1-10 alkyl, C1-10 alkoxy, haloC1-10 alkyl, C3-10 cycloalkyl, C2-12 alkenyl, C2-12 alkynyl, C6-10aryl, a 4- to 12-membered heteroaryl, a 4- to 12-membered heterocyclyl, a 4- to 12-membered heteroaryl-C1-10 alkyl, —CN, —NO2, —(CH2)m—SO2R14, —NR14SO2R14, ═O, —(CH2)m—SO2NR14R14, —(CH2)m—NR14SO2R14, —(CH2)m—NR14SO2NR14R14, —NR14SO2NR14R14, —CO2NR14R14, —NR14CO2NR14R14, —NR14COR14, —SO2NR14COR14, —SO2NR14CONR14R14, —NR14CO2R14, —CO2R14, —NR14R14, —NR14CONR14R14, —C(═NOR14)NR14R14, —CONR14OR14 or —NCOR14, wherein the alkyl, cycloalkyl, alkenyl, alkoxy, aryl, heteroaryl and heterocyclyl may be optionally substituted with one or more R14a's and the heteroaryl and heterocyclyl consist of carbon atoms and 1, 2, 3, or 4 heteroatoms independently selected from the group consisting of N, S, or O;
R13b-1, at each occurrence, is independently H, —OH, F, Cl, Br, I, C1-10 alkyl, C1-10 alkoxy, haloC1-10 alkyl, C3-10 cycloalkyl, C2-12 alkenyl, C2-12 alkynyl, C6-10aryl, a 4- to 12-membered heteroaryl, a 4- to 12-membered heterocyclyl, a 4- to 12-membered heteroaryl-C1-10 alkyl, —CN, —NO2, —(CH2)m—SO2R14, —NR14SO2R14, —O, —CONR14R14, —(CH2)m—SO2NR14R14, —(CH2)m—NR14SO2R14, —(CH2)m—NR14SO2NR14R14, —NR14SO2NR14R14, —CO2NR14R14, —NR14CO2NR14R14, —NR14COR14, —SO2NR14COR14, —SO2NR14CONR14R14, —NR14CO2R14, —CO2R14, —NR14R14, —NR14CONR14R14, —C(═NOR14)NR14R14, —CONR14OR14 or —NCOR14, wherein the alkyl, cycloalkyl, alkenyl, aryl, heteroaryl and heterocyclyl may be optionally substituted with one or more R14a's and the heteroaryl and heterocyclyl consist of carbon atoms and 1, 2, 3, or 4 heteroatoms independently selected from the group consisting of N, S, or O;
R13b-2, at each occurrence, is independently H, —OH, Cl, Br, I, C1-10 alkyl, C1-10 alkoxy, haloC2-10 alkyl, C3-10 cycloalkyl, C2-12 alkenyl, C2-12 alkynyl, C6-10aryl, a 4- to 12-membered heteroaryl, a 4- to 12-membered heterocyclyl, a 4- to 12-membered heteroaryl-C1-10 alkyl, —CN, —NO2, —(CH2)m—SO2R14, —NR14SO2R14, —O, —(CH2)m—SO2NR14R14, —(CH2)m—NR14SO2R14, —(CH2)m—NR14SO2NR14R14, —NR14SO2NR14R14, —CO2NR14R14, —NR14CO2NR14R14, —NR14COR14, —SO2NR14COR14, —SO2NR14CONR14R14, —NR14CO2R14, —CO2R14, —NR14R14, —NR14CONR14R14, —C(═NOR14)NR14R14, —CONR14OR14 or —NCOR14, wherein the alkyl, cycloalkyl, alkenyl, alkoxy, aryl, heteroaryl and heterocyclyl may be optionally substituted with one or more R14a's and the heteroaryl and heterocyclyl consist of carbon atoms and 1, 2, 3, or 4 heteroatoms independently selected from the group consisting of N, S, or O;
R13b-4, at each occurrence, is independently H, —OH, F, Cl, Br, I, C1-10 alkyl, C1-10 alkoxy, haloC1-10 alkyl, C3-10 cycloalkyl, C2-12 alkenyl, C2-12 alkynyl, C6-10aryl, a 4- to 12-membered heteroaryl, a 4- to 12-membered heterocyclyl, a 4- to 12-membered heteroaryl-C1-10 alkyl, —CN, —NO2, —(CH2)m—SO2R14, —NR14SO2R14, ═O, —CONR14R14, —(CH2)m—SO2NR14R14, —(CH2)m—NR14SO2R14, —NR14SO2NR14R14, —CO2NR14R14, —NR14CO2NR14R14, —SO2NR14COR14, —SO2NR14CONR14R14, —NR14CO2R14, —CO2R14, —NR14R14, —NR14CONR14R14, —C(═NOR14)NR14R14, —CONR14OR14 or —NCOR14, wherein the alkyl, cycloalkyl, alkenyl, alkoxy, aryl, heteroaryl and heterocyclyl may be optionally substituted with one or more R14a's and the heteroaryl and heterocyclyl consist of carbon atoms and 1, 2, 3, or 4 heteroatoms independently selected from the group consisting of N, S, or O;
R13b-5, at each occurrence, is independently H, —OH, F, Cl, Br, I, C1-10 alkyl, C1-10 alkoxy, haloC1-10 alkyl, C3-10 cycloalkyl, C2-12 alkenyl, C2-12 alkynyl, C6-10aryl, a 4- to 12-membered heteroaryl, a 4- to 12-membered heterocyclyl, a 4- to 12-membered heteroaryl-C1-10 alkyl, —CN, —NO2, —(CH2)m—SO2R14, —NR14SO2R14, ═O, —CONR14R14, —(CH2)m—SO2NR14R14, —(CH2)m—NR14SO2R14, —(CH2)m—NR14SO2NR14R14, —NR14SO2NR14R14, —CO2NR14R14, —NR14CO2NR14R14, —NR14COR14, —SO2NR14COR14, —SO2NR14CONR14R14, —NR14CO2R14, —CO2R14, —NR14R14, —NR14CONR14R14, —C(═NOR14)NR14R14, —CONR14OR14 or —NCOR14, wherein the alkyl, cycloalkyl, alkenyl, alkoxy, aryl, heteroaryl and heterocyclyl may be optionally substituted with one or more R14a's and the heteroaryl and heterocyclyl consist of carbon atoms and 1, 2, 3, or 4 heteroatoms independently selected from the group consisting of N, S, or O;
R13c, at each occurrence, is independently H, —OH, F, Cl, Br, I, C1-10 alkyl, C1-10 alkoxy, haloC1-10 alkyl, C3-10 cycloalkyl, C2-12 alkenyl, C2-12 alkynyl, C6-10aryl, a 4- to 12-membered heteroaryl, a 4- to 12-membered heterocyclyl, —CN, —NO2, —(CH2)m—SO2R14, —NR14SO2R14, ═O, —CONR14R14, —(CH2)m—SO2NR14R14, —(CH2)m—NR14SO2R14, —(CH2)m—NR14SO2NR14R14, —NR14SO2NR14R14, —(CH2)m—OCONR14R14, —CO2NR14R14, —NR14CO2NR14R14, —NR14COR14, —SO2NR14COR14, —NR14CO2R14, —CO2R26, —NR14R14, —NR14CONR14R14, —C(═NOR14)NR14R14, —CONR14OR14 or —NCOR14, wherein the alkyl, cycloalkyl, alkenyl, alkoxy, aryl, heteroaryl and heterocyclyl may be optionally substituted with one or more R14a's and the heteroaryl and heterocyclyl consist of carbon atoms and 1, 2, 3, or 4 heteroatoms independently selected from the group consisting of N, S, or O;
R13cc, at each occurrence, is independently H, F, Cl, Br, I, C1-10 alkyl, C1-10 alkoxy, haloC1-10 alkyl, C3-10 cycloalkyl, C2-12 alkenyl, C2-12 alkynyl, C6-10aryl, a 4- to 12-membered heteroaryl, a 4- to 12-membered heterocyclyl, a 4- to 12-membered heteroaryl-C1-10 alkyl, —CN, —NO2, —(CH2)m—SO2R14, —NR14SO2R14, ═O, —CONR14R14, —(CH2)m—SO2NR14R14, —(CH2)m—NR14SO2R14, —(CH2)m—NR14SO2NR14R14, —NR14SO2NR14R14, —CO2NR14R14, —NR14CO2NR14R14, —NR14COR14, —SO2NR14COR14, —SO2NR14CONR14R14, —NR14CO2R14, —CO2R14, —NR14R14, —NR14CONR14R14, —C(═NOR14)NR14R14, —CONR14OR14, or —NCOR14, wherein the alkyl, cycloalkyl, alkenyl, alkoxy, aryl, heteroaryl and heterocyclyl may be optionally substituted with one or more R14a's and the heteroaryl and heterocyclyl consist of carbon atoms and 1, 2, 3, or 4 heteroatoms independently selected from the group consisting of N, S, or O;
R13c-1, at each occurrence, is independently H, —OH, F, Cl, Br, I, C1-10 alkyl, C1-10 alkoxy, haloC2-10 alkyl, C3-10 cycloalkyl, C2-12 alkenyl, C2-12 alkynyl, C6-10aryl, a 6- to 12-membered heteroaryl, a 6- to 12-membered heterocyclyl, a 4- to 12-membered heteroaryl-C1-10 alkyl, —NO2, —NR14SO2R14, ═O, —(CH2)m—NR14SO2R14, —NR14SO2NR14R14, —CO2NR14R14, —NR14CO2NR14R14, —NR14COR14, —SO2NR14COR14, —SO2NR14CONR14R14, —NR14CO2R14, —NR14R14, —C(═NOR14)NR14R14, —CONR14OR14 or —NCOR14, wherein the alkyl, cycloalkyl, alkenyl, aryl, heteroaryl and heterocyclyl may be optionally substituted with one or more R14a's and the heteroaryl and heterocyclyl consist of carbon atoms and 1, 2, 3, or 4 heteroatoms independently selected from the group consisting of N, S, or O;
R13c-2, at each occurrence, is independently H, —OH, F, Cl, Br, I, C2-10 alkyl, C1-10 alkoxy, haloC1-10 alkyl, C3-10 cycloalkyl, C2-12 alkenyl, C2-12 alkynyl, C6-10aryl, a 4- to 12-membered heteroaryl, a 4- to 12-membered heterocyclyl, a 4- to 12-membered heteroaryl-C1-10 alkyl, —CN, —NO2, —(CH2)m—SO2R14, —NR14SO2R14, ═O, —CONR14R14, —(CH2)m—SO2NR14R14, —(CH2)m—NR14SO2R14, —(CH2)m—NR14SO2NR14R14, —NR14SO2NR14R14, —CO2NR14R14, —NR14CO2NR14R14, —NR14COR14, —SO2NR14COR14, —SO2NR14CONR14R14, —NR14CO2R14, —CO2R14, —NR14R14, —NR14CONR14R14, —C(═NOR14)NR14R14, —CONR14OR14 or —NCOR14, wherein the alkyl, cycloalkyl, alkenyl, alkoxy, aryl, heteroaryl and heterocyclyl may be optionally substituted with one or more R14a's and the heteroaryl and heterocyclyl consist of carbon atoms and 1, 2, 3, or 4 heteroatoms independently selected from the group consisting of N, S, or O;
R13c-4, at each occurrence, is independently H, —OH, Cl, Br, I, C1-10 alkyl, C1-10 alkoxy, haloC1-10 alkyl, C3-10 cycloalkyl, C2-12 alkenyl, C2-12 alkynyl, C6-10aryl, a 4- to 12-membered heteroaryl, a 4- to 12-membered heterocyclyl, a 4- to 12-membered heteroaryl-C1-10 alkyl, —CN, —NO2, —(CH2)m—SO2R14, —NR14SO2R14, ═O, —CONR14R14, —(CH2)m—SO2NR14R14, —(CH2)m—NR14SO2R14, —(CH2)m—NR14SO2NR14R14, —NR14SO2NR14R14, —CO2NR14R14, —NR14CO2NR14R14, —NR14COR14, —SO2NR14COR14, —SO2NR14CONR14R14, —NR14CO2R14, —CO2R14, —NR14R14, —NR14CONR14R14, —C(═NOR14)NR14R14, —CONR14OR14 or —NCOR14, wherein the alkyl, cycloalkyl, alkenyl, alkoxy, aryl, heteroaryl and heterocyclyl may be optionally substituted with one or more R14a's and the heteroaryl and heterocyclyl consist of carbon atoms and 1, 2, 3, or 4 heteroatoms independently selected from the group consisting of N, S, or O;
R13c-5, at each occurrence, is independently H, —OH, F, Cl, Br, I, C1-10 alkyl, C1-10 alkoxy, haloC1-10 alkyl, C3-10 cycloalkyl, C2-12 alkenyl, C2-12 alkynyl, C6-10aryl, a 4- to 12-membered heteroaryl, a 4- to 12-membered heterocyclyl, a 4- to 12-membered heteroaryl-C1-10 alkyl, —CN, —NO2, —(CH2)m—SO2R14, —NR14SO2R14, ═O, —CONR14R14, —(CH2)m—SO2NR14R14, —(CH2)m—NR14SO2R14, —(CH2)m—NR14SO2NR14R14, —NR14SO2NR14R14, —CO2NR14R14, —NR14CO2NR14R14, —NR14COR14, —SO2NR14COR14, —SO2NR14CONR14R14, —NR14CO2R14, —CO2R14, —NR14R14, —NR14CONR14R14, —C(═NOR14)NR14R14, —CONR14OR14 or —NCOR14, wherein the alkyl, cycloalkyl, alkenyl, alkoxy, aryl, heteroaryl and heterocyclyl may be optionally substituted with one or more R14a's and the heteroaryl and heterocyclyl consist of carbon atoms and 1, 2, 3, or 4 heteroatoms independently selected from the group consisting of N, S, or O;
R13d, at each occurrence, is independently H, —OH, F, Cl, Br, I, C1-10 alkyl, C2-10 alkoxy, haloC1-10 alkyl, C3-10 cycloalkyl, C2-12 alkenyl, C2-12 alkynyl, C6-10aryl, a 4- to 12-membered heteroaryl, a 4- to 12-membered heterocyclyl, a 4- to 12-membered heteroaryl-C1-10 alkyl, —CN, —NO2, —(CH2)m—SO2R14, —NR14SO2R14, —O, —CONR14R14, —(CH2)m—SO2NR14R14, —(CH2)m—NR14SO2R14, —(CH2)m—NR14SO2NR14R14, —NR14SO2NR14R14, —CO2NR14R14, —NR14CO2NR14R14, —NR14COR14, —SO2NR14COR14, —SO2NR14CONR14R14, —NR14CO2R14, —CO2R14, —NR14R14, —NR14CONR14R14, —C(═NOR14)NR14R14, —CONR14OR14 or —NCOR14, wherein the alkyl, cycloalkyl, alkenyl, alkoxy, aryl, heteroaryl and heterocyclyl may be optionally substituted with one or more R14a's and the heteroaryl and heterocyclyl consist of carbon atoms and 1, 2, 3, or 4 heteroatoms independently selected from the group consisting of N, S, or O;
R13dd, at each occurrence, is independently H, —OH, F, Cl, Br, I, C1-10 alkyl, C1-10 alkoxy, haloC1-10 alkyl, C3-10 cycloalkyl, C2-12 alkenyl, C2-12 alkynyl, C6-10aryl, a 4- to 12-membered heteroaryl, a 4- to 12-membered heterocyclyl, a 4- to 12-membered heteroaryl-C1-10 alkyl, —CN, —NO2, —(CH2)m—SO2R14, —NR14SO2R14, ═O, —CONR14R14, —(CH2)m—SO2NR14R14, —(CH2)m—NR14SO2R14, —(CH2)m—NR14SO2NR14R14, —NR14SO2NR14R14, —CO2NR14R14, —NR14CO2NR14R14, —NR14COR14, —SO2NR14COR14, —SO2NR14CONR14R14, —NR14CO2R14, —CO2R14, —NR14R14, —NR14CONR14R14, —C(═NOR14)NR14R14, —CONR14OR14 or —NCOR14, wherein the alkyl, cycloalkyl, alkenyl, alkoxy, aryl, heteroaryl and heterocyclyl may be optionally substituted with one or more R14a's and the heteroaryl and heterocyclyl consist of carbon atoms and 1, 2, 3, or 4 heteroatoms independently selected from the group consisting of N, S, or O;
R13d-1, at each occurrence, is independently H, —OH, F, Cl, Br, I, C1-10 alkyl, C1-10 alkoxy, haloC2-10 alkyl, C3-10 cycloalkyl, C2-12 alkenyl, C2-12 alkynyl, C6-10aryl, a 4- to 12-membered heteroaryl, a 4- to 12-membered heterocyclyl, a 4- to 12-membered heteroaryl-C1-10 alkyl, —CN, —NO2, —NR14SO2R14, ═O, —CONR14R14, —(CH2)m—SO2NR14R14, —(CH2)m—NR14SO2R14, —(CH2)m—NR14SO2NR14R14, —NR14SO2NR14R14, —CO2NR14R14, —NR14CO2NR14R14, —NR14COR14, —SO2NR14COR14, —SO2NR14CONR14R14, —NR14CO2R14, —CO2R14, —NR14CONR14R14, —C(═NOR14)NR14R14, —CONR14OR14 or —NCOR14, wherein the alkyl, cycloalkyl, alkenyl, aryl, heteroaryl and heterocyclyl may be optionally substituted with one or more R14a's and the heteroaryl and heterocyclyl consist of carbon atoms and 1, 2, 3, or 4 heteroatoms independently selected from the group consisting of N, S, or O;
R13d-2, at each occurrence, is independently H, —OH, Cl, Br, I, C1-10 alkyl, C1-10 alkoxy, haloC1-10 alkyl, C3-10 cycloalkyl, C2-12 alkenyl, C2-12 alkynyl, C6-10aryl, a 4- to 12-membered heteroaryl, a 4- to 12-membered heterocyclyl, a 4- to 12-membered heteroaryl-C1-10 alkyl, —CN, —NO2, —(CH2)m—SO2R14, —NR14SO2R14, ═O, —CONR14R14, —(CH2)m—SO2NR14R14, —(CH2)m—NR14SO2R14, —(CH2)m—NR14SO2NR14R14, —NR14SO2NR14R14, —CO2NR14R14, —NR14CO2NR14R14, —NR14COR14, —SO2NR14COR14, —SO2NR14CONR14R14, —NR14CO2R14, —CO2R14, —NR14R14, —NR14CONR14R14, —C(═NOR14)NR14R14, —CONR14OR14 or —NCOR14, wherein the alkyl, cycloalkyl, alkenyl, alkoxy, aryl, heteroaryl and heterocyclyl may be optionally substituted with one or more R14a's and the heteroaryl and heterocyclyl consist of carbon atoms and 1, 2, 3, or 4 heteroatoms independently selected from the group consisting of N, S, or O;
R13d-4, at each occurrence, is independently H, —OH, F, Cl, Br, I, C1-10 alkyl, C1-10 alkoxy, haloC1-10 alkyl, C3-10 cycloalkyl, C2-12 alkenyl, C2-12 alkynyl, C6-10aryl, a 4- to 12-membered heteroaryl, a 4- to 12-membered heterocyclyl, a 4- to 12-membered heteroaryl-C1-10 alkyl, —CN, —NO2, —(CH2)m—SO2R14, —NR14SO2R14, ═O, —CONR14R14, —(CH2)m—SO2NR14R14, —(CH2)m—NR14SO2R14, —(CH2)m—NR14SO2NR14R14, —NR14SO2NR14R14, —CO2NR14R14, —NR14CO2NR14R14, —NR14COR14, —SO2NR14COR14, —SO2NR14CONR14R14, —NR14CO2R14, —CO2R14, —NR14R14, —NR14CONR14R14, —C(═NOR14)NR14R14, —CONR14OR14 or —NCOR14, wherein the alkyl, cycloalkyl, alkenyl, alkoxy, aryl, heteroaryl and heterocyclyl may be optionally substituted with one or more R14a's and the heteroaryl and heterocyclyl consist of carbon atoms and 1, 2, 3, or 4 heteroatoms independently selected from the group consisting of N, S, or O;
R13e, at each occurrence, is independently H, —OH, F, Cl, Br, I, C1-10 alkyl, C1-10 alkoxy, haloC1-10 alkyl, C3-10 cycloalkyl, C2-12 alkenyl, C2-12 alkynyl, C6-10aryl, a 4- to 12-membered heteroaryl, a 4- to 12-membered heterocyclyl, a 4- to 12-membered heteroaryl-C1-10 alkyl, —CN, —NO2, —(CH2)m—SO2R14, ═O, —CONR14R14, —(CH2)m—SO2NR14R14, —(CH2)m—NR14SO2R14, —(CH2).—NR14SO2NR14R14, —NR14SO2NR14R14, —CO2NR14R14, —NR14CO2NR14R14, —NR14COR14, —SO2NR14COR14, —SO2NR14CONR14R14, —NR14CO2R14, —CO2R14, —NR14R14, —NR14CONR14R14, —C(═NOR14)NR14R14, —CONR14OR14 or —NCOR14, wherein the alkyl, cycloalkyl, alkenyl, alkoxy, aryl, heteroaryl and heterocyclyl may be optionally substituted with one or more R14a's and the heteroaryl and heterocyclyl consist of carbon atoms and 1, 2, 3, or 4 heteroatoms independently selected from the group consisting of N, S, or O;
R13ee, at each occurrence, is independently H, —OH, F, Cl, Br, I, C1-10 alkyl, C1-10 alkoxy, haloC1-10 alkyl, C3-10 cycloalkyl, C2-12 alkenyl, C2-12 alkynyl, C6-10aryl, a 4- to 12-membered heteroaryl, a 4- to 12-membered heterocyclyl, a 4- to 12-membered heteroaryl-C1-10 alkyl, —CN, —NO2, —(CH2)m—SO2R14, —NR14SO2R14, —O, —CONR14R14, —(CH2)m—SO2NR14R14, —(CH2)m—NR14SO2R14, —(CH2)m—NR14SO2NR14R14, —NR14SO2NR14R14, —CO2NR14R14, —NR14CO2NR14R14, —NR14COR14, —SO2NR14COR14, —SO2NR14CONR14R14, —NR14CO2R14, —CO2R14, —NR14R14, —NR14CONR14R14, —C(═NOR14)NR14R14, —CONR14OR14 or —NCOR14, wherein the alkyl, cycloalkyl, alkenyl, alkoxy, aryl, heteroaryl and heterocyclyl may be optionally substituted with one or more R14a's and the heteroaryl and heterocyclyl consist of carbon atoms and 1, 2, 3, or 4 heteroatoms independently selected from the group consisting of N, S, or O;
R13e-1, at each occurrence, is independently H, —OH, Cl, Br, I, C1-10 alkyl, C1-10 alkoxy, haloC2-10 alkyl, C3-10 cycloalkyl, C2-12 alkenyl, C2-12 alkynyl, C6-10aryl, a 4- to 12-membered heteroaryl, a 4- to 12-membered heterocyclyl, a 4- to 12-membered heteroaryl-C1-10 alkyl, —CN, —NO2, —(CH2)m—SO2R14, —NR14SO2R14, —O, —(CH2)m—SO2NR14R14, —(CH2)m—NR14SO2R14, —(CH2)m—NR14SO2NR14R14, —NR14SO2NR14R14, —CO2NR14R14, —NR14CO2NR14R14, —SO2NR14COR14, —SO2NR14CONR14R14, —NR14CO2R14, —CO2R14, —NR14R14, —NR14CONR14R14, —C(═NOR14)NR14R14, —CONR14OR14 or —NCOR14, wherein the alkyl, cycloalkyl, alkenyl, alkoxy, aryl, heteroaryl and heterocyclyl may be optionally substituted with one or more R14a's and the heteroaryl and heterocyclyl consist of carbon atoms and 1, 2, 3, or 4 heteroatoms independently selected from the group consisting of N, S, or O;
R13e-2, at each occurrence, is independently H, —OH, F, Cl, Br, I, C1-10 alkyl, C1-10 alkoxy, haloC1-10 alkyl, C3-10 cycloalkyl, C2-12 alkenyl, C2-12 alkynyl, C6-10aryl, a 4- to 12-membered heteroaryl, a 4- to 12-membered heterocyclyl, a 4- to 12-membered heteroaryl-C1-10 alkyl, —CN, —NO2, —(CH2)m—SO2R14, —NR14SO2R14, ═O, —CONR14R14, —(CH2)m—SO2NR14R14, —(CH2)m—NR14SO2R14, —(CH2)m—NR14SO2NR14R14, —NR14SO2NR14R14, —CO2NR14R14, —NR14CO2NR14R14, —NR14COR14, —SO2NR14COR14, —SO2NR14CONR14R14, —NR14CO2R14, —CO2R14, —NR14R14, —NR14CONR14R14, —C(═NOR14)NR14R14, —CONR14OR14 or —NCOR14, wherein the alkyl, cycloalkyl, alkenyl, alkoxy, aryl, heteroaryl and heterocyclyl may be optionally substituted with one or more R14a's and the heteroaryl and heterocyclyl consist of carbon atoms and 1, 2, 3, or 4 heteroatoms independently selected from the group consisting of N, S, or O;
R13f, at each occurrence, is independently H, —OH, F, Cl, Br, I, C1-10 alkyl, C2-10 alkoxy, haloC1-10 alkyl, C3-10 cycloalkyl, C2-12 alkenyl, C2-12 alkynyl, C6-10aryl, a 4- to 12-membered heteroaryl, a 4- to 12-membered heteroaryl-C1-10 alkyl, —CN, —NO2, —(CH2)m—SO2R14, —NR14SO2R14, —CONR14R14, —(CH2)m—SO2NR14R14, —(CH2)m—NR14SO2R14, —(CH2)m—NR14SO2NR14R14, —NR14SO2NR14R14, —CO2NR14R14, —NR14CO2NR14R14, —NR14COR14, —SO2NR14COR14, —SO2NR14CONR14R14, —NR14CO2R14, —CO2R14, —NR14R14, —NR14CONR14R14, —C(═NOR14)NR14R14, —CONR14OR14 or —NCOR14, wherein the alkyl, cycloalkyl, alkenyl, alkoxy, aryl, heteroaryl and heterocyclyl may be optionally substituted with one or more R14a's and the heteroaryl and heterocyclyl consist of carbon atoms and 1, 2, 3, or 4 heteroatoms independently selected from the group consisting of N, S, or O;
R13g, at each occurrence, is independently H, —OH, F, Cl, Br, I, C1-10 alkyl, C1-10 alkoxy, haloC1-10 alkyl, C3-10 cycloalkyl, C2-12 alkenyl, C2-12 alkynyl, C6-10aryl, a 4- to 12-membered heteroaryl, a 4- to 12-membered heterocyclyl, a 4- to 12-membered heteroaryl-C1-10 alkyl, —CN, —NO2, —(CH2)m—SO2R14, —NR14SO2R14, —O, —CONR14R14, —(CH2)m—SO2NR14R14, —(CH2)m—NR14SO2R14, —(CH2)m—NR14SO2NR14R14, —NR14SO2NR14R14, —CO2NR14R14, —NR14CO2NR14R14, —NR14COR14, —SO2NR14COR14, —SO2NR14CONR14R14, —NR14CO2R14, —CO2R14, —NR14R14, —NR14CONR14R14, —C(═NOR14)NR14R14, —CONR14OR14 or —NCOR14, wherein the alkyl, cycloalkyl, alkenyl, alkoxy, aryl, heteroaryl and heterocyclyl may be optionally substituted with one or more R14a's and the heteroaryl and heterocyclyl consist of carbon atoms and 1, 2, 3, or 4 heteroatoms independently selected from the group consisting of N, S, or O;
R13g-2, at each occurrence, is independently H, —OH, F, Cl, Br, I, C2-10 alkyl, C1-10 alkoxy, haloC1-10 alkyl, C3-10 cycloalkyl, C2-12 alkenyl, C2-12 alkynyl, C6-10aryl, a 4- to 12-membered heteroaryl, a 4- to 12-membered heterocyclyl, a 4- to 12-membered heteroaryl-C1-10 alkyl, —CN, —NO2, —(CH2)m—SO2R14, —NR14SO2R14, ═O, —CONR14R14, —(CH2)m—SO2NR14R14, —(CH2)m—NR14SO2R14, —(CH2)m—NR14SO2NR14R14, —NR14SO2NR14R14, —CO2NR14R14, —NR14CO2NR14R14, —NR14COR14, —SO2NR14COR14, —SO2NR14CONR14R14, —NR14CO2R14, —CO2R14, —NR14R14, —NR14CONR14R14, —C(═NOR14)NR14R14, —CONR14OR14 or —NCOR14, wherein the alkyl, cycloalkyl, alkenyl, alkoxy, aryl, heteroaryl and heterocyclyl may be optionally substituted with one or more R14a's and the heteroaryl and heterocyclyl consist of carbon atoms and 1, 2, 3, or 4 heteroatoms independently selected from the group consisting of N, S, or O;
R13h, at each occurrence, is independently H, —OH, F, Cl, Br, I, C1-10 alkyl, C1-10 alkoxy, haloC1-10 alkyl, C3-10 cycloalkyl, C2-12 alkenyl, C2-12 alkynyl, C6-10aryl, a 4- to 12-membered heteroaryl, a 4- to 12-membered heterocyclyl, a 4- to 12-membered heteroaryl-C1-10 alkyl, —CN, —NO2, —(CH2)m—SO2R14, —NR14SO2R14, —O, —CONR14R14, —(CH2)m—SO2NR14R14, —(CH2)m—NR14SO2R14, —(CH2)m—NR14SO2NR14R14, —NR14SO2NR14R14, —CO2NR14R14, —NR14CO2NR14R14, —NR14COR14, —SO2NR14COR14, —SO2NR14CONR14R14, —NR14CO2R14, —CO2R14, —NR14R14, —NR14CONR14R14, —C(═NOR14)NR14R14, —CONR14OR14 or —NCOR14, wherein the alkyl, cycloalkyl, alkenyl, alkoxy, aryl, heteroaryl and heterocyclyl may be optionally substituted with one or more R14a's and the heteroaryl and heterocyclyl consist of carbon atoms and 1, 2, 3, or 4 heteroatoms independently selected from the group consisting of N, S, or O;
R13h-1, at each occurrence, is independently H, —OH, F, Cl, Br, I, C1-10 alkyl, C1-10 alkoxy, haloC1-10 alkyl, C3-10 cycloalkyl, C2-12 alkenyl, C2-12 alkynyl, C7-10aryl, a 4- to 12-membered heteroaryl, a 4- to 12-membered heterocyclyl, a 4- to 12-membered heteroaryl-C1-10 alkyl, —CN, —NO2, —(CH2)m—SO2R14, —NR14SO2R14, ═O, —CONR14R14, —(CH2)m—SO2NR14R14, —(CH2)m—NR14SO2R14, —(CH2)m—NR14SO2NR14R14, —NR14SO2NR14R14, —CO2NR14R14, —NR14CO2NR14R14, —NR14COR14, —SO2NR14COR14, —SO2NR14CONR14R14, —NR14CO2R14, —CO2R14, —NR14R14, —NR14CONR14R14, —C(═NOR14)NR14R14, —CONR14OR14 or —NCOR14, wherein the alkyl, cycloalkyl, alkenyl, alkoxy, aryl, heteroaryl and heterocyclyl may be optionally substituted with one or more R14a's and the heteroaryl and heterocyclyl consist of carbon atoms and 1, 2, 3, or 4 heteroatoms independently selected from the group consisting of N, S, or O;
R13hh, at each occurrence, is independently H, —OH, F, Cl, Br, I, C1-10 alkyl, C1-10 alkoxy, haloC1-10 alkyl, C3-10 cycloalkyl, C2-12 alkenyl, C2-12 alkynyl, C6-10aryl, a 4- to 12-membered heteroaryl, a 4- to 12-membered heterocyclyl, a 4- to 12-membered heteroaryl-C1-10 alkyl, —CN, —NO2, —(CH2)m—SO2R14, —NR14SO2R14, ═O, —CONR14R14, —(CH2)m—SO2NR14R14, —(CH2)m—NR14SO2R14, —(CH2)m—NR14SO2NR14R14, —NR14SO2NR14R14, —CO2NR14R14, —NR14CO2NR14R14, —NR14COR14, —SO2NR14COR14, —SO2NR14CONR14R14, —NR14CO2R14, —CO2R14, —NR14R14, —NR14CONR14R14, —C(═NOR14)NR14R14, —CONR14OR14 or —NCOR14, wherein the alkyl, cycloalkyl, alkenyl, alkoxy, aryl, heteroaryl and heterocyclyl may be optionally substituted with one or more R14a's and the heteroaryl and heterocyclyl consist of carbon atoms and 1, 2, 3, or 4 heteroatoms independently selected from the group consisting of N, S, or O;
R13hh-1, at each occurrence, is independently H, —OH, F, Cl, Br, I, C2-10 alkyl, C1-10 alkoxy, haloC1-10 alkyl, C3-10 cycloalkyl, C2-12 alkenyl, C2-12 alkynyl, C6-10aryl, a 4- to 12-membered heteroaryl, a 4- to 12-membered heterocyclyl, a 4- to 12-membered heteroaryl-C1-10 alkyl, —CN, —NO2, —(CH2)m—SO2R14, —NR14SO2R14, ═O, —CONR14R14, —(CH2)m—SO2NR14R14, —(CH2)m—NR14SO2R14, —(CH2)m—NR14SO2NR14R14, —NR14SO2NR14R14, —CO2NR14R14, —NR14CO2NR14R14, —NR14COR14, —SO2NR14COR14, —SO2NR14CONR14R14, —NR14CO2R14, —CO2R14, —NR14R14, —NR14CONR14R14, —C(═NOR14)NR14R14, —CONR14OR14 or —NCOR14, wherein the alkyl, cycloalkyl, alkenyl, alkoxy, aryl, heteroaryl and heterocyclyl may be optionally substituted with one or more R14a's and the heteroaryl and heterocyclyl consist of carbon atoms and 1, 2, 3, or 4 heteroatoms independently selected from the group consisting of N, S, or O;
R13hh-2, at each occurrence, is independently H, —OH, F, Cl, Br, I, C1-10 alkyl, C1-10 alkoxy, haloC1-10 alkyl, C3-10 cycloalkyl, C2-12 alkenyl, C2-12 alkynyl, C6-10aryl, a 4- to 12-membered heteroaryl, a 4- to 12-membered heterocyclyl, a 4- to 12-membered heteroaryl-C1-10 alkyl, —CN, —NO2, —(CH2)m—SO2R14, —NR14SO2R14, —O, —CONR14R14, —(CH2)m—SO2NR14R14, —(CH2)m—NR14SO2R14, —(CH2)m—NR14SO2NR14R14, —NR14SO2NR14R14, —CO2NR14R14, —NR14CO2NR14R14, —NR14COR14, —SO2NR14COR14, —SO2NR14CONR14R14, —NR14CO2R14, —CO2R14, —NR14R14, —NR14CONR14R14, —C(═NOR14)NR14R14, —CONR14OR14 or —NCOR14, wherein the alkyl, cycloalkyl, alkenyl, alkoxy, aryl, heteroaryl and heterocyclyl may be optionally substituted with one or more R14a's and the heteroaryl and heterocyclyl consist of carbon atoms and 1, 2, 3, or 4 heteroatoms independently selected from the group consisting of N, S, or O;
R13j, at each occurrence, is independently H, —OH, F, Cl, Br, I, C1-10 alkyl, C1-10 alkoxy, haloC1-10 alkyl, C3-10 cycloalkyl, C2-12 alkenyl, C2-12 alkynyl, C6-10aryl, a 4- to 12-membered heteroaryl, a 4- to 12-membered heterocyclyl, a 4- to 12-membered heteroaryl-C1-10 alkyl, —CN, —NO2, —(CH2)m—SO2R14, ═O, —CONR14R14, —(CH2)m—SO2NR14R14, —(CH2)m—NR14SO2R14, —(CH2)m—NR14SO2NR14R14, —NR14SO2NR14R14, —CO2NR14R14, —NR14CO2NR14R14, —NR14COR14, —SO2NR14COR14, —SO2NR14CONR14R14, —NR14CO2R14, —CO2R14, —NR14R14, —NR14CONR14R14, —C(═NOR14)NR14R14, —CONR14OR14 or —NCOR14, wherein the alkyl, cycloalkyl, alkenyl, alkoxy, aryl, heteroaryl and heterocyclyl may be optionally substituted with one or more R14a's and the heteroaryl and heterocyclyl consist of carbon atoms and 1, 2, 3, or 4 heteroatoms independently selected from the group consisting of N, S, or O;
R13m, at each occurrence, is independently H, —OH, F, Cl, Br, I, C1-10 alkyl, C1-10 alkoxy, haloC1-10 alkyl, C3-10 cycloalkyl, C2-12 alkenyl, C2-12 alkynyl, C6-10aryl, a 4- to 12-membered heteroaryl, a 4- to 12-membered heterocyclyl, a 4- to 12-membered heteroaryl-C1-10 alkyl, —CN, —NO2, —(CH2)m—SO2R14, —NR14SO2R14, —O, —CONR14R14, —(CH2)m—SO2NR14R14, —(CH2)m—NR14SO2R14, —(CH2)m—NR14SO2NR14R14, —NR14SO2NR14R14, —CO2NR14R14, —NR14CO2NR14R14, —NR14COR14, —SO2NR14COR14, —SO2NR14CONR14R14, —NR14CO2R14, —CO2R14, —NR14R14, —NR14CONR14R14, —C(═NOR14)NR14R14, —CONR14OR14 or —NCOR14, wherein the alkyl, cycloalkyl, alkenyl, alkoxy, aryl, heteroaryl and heterocyclyl may be optionally substituted with one or more R14a's and the heteroaryl and heterocyclyl consist of carbon atoms and 1, 2, 3, or 4 heteroatoms independently selected from the group consisting of N, S, or O;
R13m-1, at each occurrence, is independently H, —OH, F, Cl, Br, I, C1-10 alkyl, C1-10 alkoxy, haloC1-10 alkyl, C3-10 cycloalkyl, C2-12 alkenyl, C2-12 alkynyl, C6-10aryl, a 4- to 12-membered heteroaryl, a 4- to 12-membered heterocyclyl, a 4- to 12-membered heteroaryl-C1-10 alkyl, —CN, —NO2, —(CH2)m—SO2R14, —NR14SO2R14, ═O, —CONR14R14, —(CH2)m—SO2NR14R14, —(CH2)m—NR14SO2R14, —(CH2)m—NR14SO2NR14R14, —NR14SO2NR14R14, —CO2NR14R14, —NR14CO2NR14R14, —NR14COR14, —SO2NR14COR14, —SO2NR14CONR14R14, —NR14CO2R14, —CO2R14, —NR14R14, —NR14CONR14R14, —C(═NOR14)NR14R14, —CONR14OR14 or —NCOR14, wherein the alkyl, cycloalkyl, alkenyl, alkoxy, aryl, heteroaryl and heterocyclyl may be optionally substituted with one or more R14a's and the heteroaryl and heterocyclyl consist of carbon atoms and 1, 2, 3, or 4 heteroatoms independently selected from the group consisting of N, S, or O;
R13n-1, at each occurrence, is independently H, —OH, F, Cl, Br, I, C2-10 alkyl, C1-10 alkoxy, haloC1-10 alkyl, C3-10 cycloalkyl, C2-12 alkenyl, C2-12 alkynyl, C6-10aryl, a 4- to 12-membered heteroaryl, a 4- to 12-membered heterocyclyl, a 4- to 12-membered heteroaryl-C1-10 alkyl, —CN, —NO2, —(CH2)m—SO2R14, —NR14SO2R14, ═O, —CONR14R14, —(CH2)m—SO2NR14R14, —(CH2)m—NR14SO2R14, —(CH2)m—NR14SO2NR14R14, —NR14SO2NR14R14, —CO2NR14R14, —NR14CO2NR14R14, —NR14COR14, —SO2NR14COR14, —SO2NR14CONR14R14, —NR14CO2R14, —CO2R14, —NR14R14, —NR14CONR14R14, —C(═NOR14)NR14R14, —CONR14OR14 or —NCOR14, wherein the alkyl, cycloalkyl, alkenyl, alkoxy, aryl, heteroaryl and heterocyclyl may be optionally substituted with one or more R14a's and the heteroaryl and heterocyclyl consist of carbon atoms and 1, 2, 3, or 4 heteroatoms independently selected from the group consisting of N, S, or O;
R13p, at each occurrence, is independently H, —OH, F, Cl, Br, I, C1-10 alkyl, C1-10 alkoxy, haloC1-10 alkyl, C3-10 cycloalkyl, C2-12 alkenyl, C2-12 alkynyl, C6-10aryl, a 4- to 12-membered heteroaryl, a 4- to 12-membered heterocyclyl, a 4- to 12-membered heteroaryl-C1-10 alkyl, —CN, —NO2, —(CH2)m—SO2R14, —NR14SO2R14, ═O, —CONR14R14, —(CH2)m—SO2NR14R14, —(CH2)m NR14SO2R14, —(CH2)m—NR14SO2NR14R14, —NR14SO2NR14R14, —CO2NR14R14, —NR14CO2NR14R14, —NR14COR14, —SO2NR14COR14, —SO2NR14CONR14R14, —NR14CO2R14, —CO2R14, —NR14R14, —NR14CONR14R14, —C(═NOR14)NR14R14, —CONR14OR14 or —NCOR14, wherein the alkyl, cycloalkyl, alkenyl, alkoxy, aryl, heteroaryl and heterocyclyl may be optionally substituted with one or more R14a's and the heteroaryl and heterocyclyl consist of carbon atoms and 1, 2, 3, or 4 heteroatoms independently selected from the group consisting of N, S, or O;
R13p-1, at each occurrence, is independently H, —OH, F, Cl, Br, I, C1-10 alkyl, C1-10 alkoxy, haloC1-10 alkyl, C3-10 cycloalkyl, C2-12 alkenyl, C2-12 alkynyl, C6-10aryl, a 4- to 12-membered heteroaryl, a 4- to 12-membered heterocyclyl, a 4- to 12-membered heteroaryl-C1-10 alkyl, —CN, —NO2, —(CH2)m—SO2R14, —NR14SO2R14, —O, —CONR14R14, —(CH2)m—SO2NR14R14, —(CH2)m—NR14SO2R14, —(CH2)m—NR14SO2NR14R14, —NR14SO2NR14R14, —CO2NR14R14, —NR14CO2NR14R14, —NR14COR14, —SO2NR14COR14, —SO2NR14CONR14R14, —NR14CO2R14, —CO2R14, —NR14R14, —NR14CONR14R14, —C(═NOR14)NR14R14, —CONR14OR14 or —NCOR14, wherein the alkyl, cycloalkyl, alkenyl, alkoxy, aryl, heteroaryl and heterocyclyl may be optionally substituted with one or more R14a's and the heteroaryl and heterocyclyl consist of carbon atoms and 1, 2, 3, or 4 heteroatoms independently selected from the group consisting of N, S, or O;
R13p-2, at each occurrence, is independently H, —OH, F, Cl, Br, I, C1-10 alkyl, C1-10 alkoxy, haloC1-10 alkyl, C3-10 cycloalkyl, C2-12 alkenyl, C2-12 alkynyl, C6-10aryl, a 4- to 12-membered heteroaryl, a 4- to 12-membered heterocyclyl, a 4- to 12-membered heteroaryl-C1-10 alkyl, —CN, —NO2, —(CH2)m—SO2R14, —NR14SO2R14, ═O, —CONR14R14, —(CH2)m—SO2NR14R14, —(CH2)m—NR14SO2R14, —(CH2)m—NR14SO2NR14R14, —NR14SO2NR14R14, —CO2NR14R14, —NR14CO2NR14R14, —NR14COR14, —SO2NR14COR14, —SO2NR14CONR14R14, —NR14CO2R14, —CO2R14, —NR14R14, —NR14CONR14R14, —C(═NOR14)NR14R14, —CONR14OR14 or —NCOR14, wherein the alkyl, cycloalkyl, alkenyl, alkoxy, aryl, heteroaryl and heterocyclyl may be optionally substituted with one or more R14a's and the heteroaryl and heterocyclyl consist of carbon atoms and 1, 2, 3, or 4 heteroatoms independently selected from the group consisting of N, S, or O;
R13q, at each occurrence, is independently H, —OH, F, Cl, Br, I, C2-10 alkyl, C1-10 alkoxy, haloC2-10 alkyl, C3-10 cycloalkyl, C2-12 alkenyl, C2-12 alkynyl, C6-10aryl, a 4- to 12-membered heteroaryl, a 4- to 12-membered heterocyclyl, a 4- to 12-membered heteroaryl-C1-10 alkyl, —CN, —NO2, —(CH2)m—SO2R14, —NR14SO2R14, ═O, —CONR14R14, —(CH2)m—SO2NR14R14, —(CH2)m—NR14SO2R14, —(CH2)m—NR14SO2NR14R14, —NR14SO2NR14R14, —CO2NR14R14, —NR14CO2NR14R14, —NR14COR14, —SO2NR14COR14, —SO2NR14CONR14R14, —NR14CO2R14, —CO2R14, —NR14R14, —NR14CONR14R14, —C(═NOR14)NR14R14, —CONR14OR14 or —NCOR14, wherein the alkyl, cycloalkyl, alkenyl, alkoxy, aryl, heteroaryl and heterocyclyl may be optionally substituted with one or more R14a's and the heteroaryl and heterocyclyl consist of carbon atoms and 1, 2, 3, or 4 heteroatoms independently selected from the group consisting of N, S, or O;
R13q-1, at each occurrence, is independently H, —OH, F, Cl, Br, I, C1-10 alkyl, C1-10 alkoxy, haloC1-10 alkyl, C3-10 cycloalkyl, C2-12 alkenyl, C2-12 alkynyl, C6-10aryl, a 4- to 12-membered heteroaryl, a 4- to 12-membered heterocyclyl, a 4- to 12-membered heteroaryl-C1-10 alkyl, —CN, —NO2, —(CH2)m—SO2R14, —NR14SO2R14, ═O, —CONR14R14, —(CH2)m—SO2NR14R14, —(CH2)m—NR14SO2R14, —(CH2)m—NR14SO2NR14R14, —NR14SO2NR14R14, —CO2NR14R14, —NR14CO2NR14R14, —NR14COR14, —SO2NR14COR14, —SO2NR14CONR14R14, —NR14CO2R14, —CO2R14, —NR14R14, —NR14CONR14R14, —C(═NOR14)NR14R14, —CONR14OR14 or —NCOR14, wherein the alkyl, cycloalkyl, alkenyl, alkoxy, aryl, heteroaryl and heterocyclyl may be optionally substituted with one or more R14a's and the heteroaryl and heterocyclyl consist of carbon atoms and 1, 2, 3, or 4 heteroatoms independently selected from the group consisting of N, S, or O;
R13q-2, at each occurrence, is independently H, —OH, F, Cl, Br, I, C1-10 alkyl, C1-10 alkoxy, haloC1-10 alkyl, C3-10 cycloalkyl, C2-12 alkenyl, C2-12 alkynyl, C6-10aryl, a 4- to 12-membered heteroaryl, a 4- to 12-membered heterocyclyl, a 4- to 12-membered heteroaryl-C1-10 alkyl, —CN, —NO2, —(CH2)m—SO2R14, —NR14SO2R14, —CONR14R14, —(CH2)m—SO2NR14R14, —(CH2)m—NR14SO2R14, —(CH2)m—NR14SO2NR14R14, —NR14SO2NR14R14, —CO2NR14R14, —NR14CO2NR14R14, —NR14COR14, —SO2NR14COR14, —SO2NR14CONR14R14, —NR14CO2R14, —CO2R14, —NR14R14, —NR14CONR14R14, —C(═NOR14)NR14R14, —CONR14OR14 or —NCOR14, wherein the alkyl, cycloalkyl, alkenyl, alkoxy, aryl, heteroaryl and heterocyclyl may be optionally substituted with one or more R14a's and the heteroaryl and heterocyclyl consist of carbon atoms and 1, 2, 3, or 4 heteroatoms independently selected from the group consisting of N, S, or O;
R14, at each occurrence, is independently selected from hydrogen, C1-10 alkyl, C3-10 cycloalkyl, C6-10 aryl, a 4- to 12-membered heteroaryl or a 4- to 12-membered heterocyclyl, wherein the alkyl, cycloalkyl, aryl, heteroaryl and heterocyclyl may be optionally substituted with be optionally substituted with 0-3 R14a and the heteroaryl and heterocyclyl consist of carbon atoms and 1, 2, 3, or 4 heteroatoms independently selected from the group consisting of N, S, or O;
or
two R14's are taken together with the atoms to which they are attached to form a cyclic ring, wherein the cyclic ring may be optionally substituted with one or more R24a's and optionally contain 1, 2, 3, or 4 heteroatoms independently selected from the group consisting of N, S, or O;
R14a, at each occurrence, is independently selected from F, Cl, Br, I, C1-10 alkyl, haloC1-10alkyl, C6-10aryl, C3-10cycloalkyl, a 4- to 12-membered heteroaryl, a 4- to 12-membered heterocyclyl, F, Cl, Br, I, —CN, —NO2, —CO2R26, —CO2NR24R24, —OCF3, —OR25, —O, —CONR24R24, —COR24, —SO2R24, —NR24R24, —NR24CO2R24, —SO2NR24R24, or C6-10 arylC1-10 alkyl, wherein the heteroaryl and heterocyclyl consist of carbon atoms and 1, 2, 3, or 4 heteroatoms independently selected from the group consisting of N, S, or O;
R24, at each occurrence, is independently selected from hydrogen, C1-10alkyl, C3-10cycloalkyl, C6-10aryl, a 4- to 12-membered heteroaryl or 4- to 12-membered heterocyclyl, wherein the alkyl, aryl, heteroaryl and heterocyclyl may be optionally substituted with one or more R24a's and the heteroaryl and heterocyclyl consist of carbon atoms and 1, 2, 3, or 4 heteroatoms independently selected from the group consisting of N, S, or O;
or
two R24's are taken together with the atoms to which they are attached to form a cyclic ring, wherein the cyclic ring may be optionally substituted with one or more R24a's and optionally contain 1, 2, 3, or 4 heteroatoms independently selected from the group consisting of N, S, or O;
R24a, at each occurrence, is independently selected from F, Cl, Br, I, C1-10 alkyl, haloC1-10alkyl, C6-10aryl, C3-10cycloalkyl, a 4- to 12-membered heteroaryl, a 4- to 12-membered heterocyclyl, —CN, —NO2, —CO2R25, —OCF3, —OR25, ═O, —CONR25R25, —COR25, —NR25R25, —NR25CO2R25, or C6-10arylC1-10alkyl, wherein the heteroaryl and heterocyclyl consist of carbon atoms and 1, 2, 3, or 4 heteroatoms independently selected from the group consisting of N, S, or O;
R24b, at each occurrence, is independently selected from C1-10 alkyl, C6-10aryl, C3-10cycloalkyl, a 4- to 12-membered heteroaryl, a 4- to 12-membered heterocyclyl, —CO2R25, —SO2NR25R25, —COR25 or C6-10arylC1-10alkyl, wherein the heteroaryl and heterocyclyl consist of carbon atoms and 1, 2, 3, or 4 heteroatoms independently selected from the group consisting of N, S, or O;
R25, at each occurrence, is independently selected from hydrogen, C1-10alkyl, C3-10cycloalkyl, C6-10aryl, a 4- to 12-membered heteroaryl or 4- to 12-membered heterocyclyl, wherein the heteroaryl and heterocyclyl consist of carbon atoms and 1, 2, 3, or 4 heteroatoms independently selected from the group consisting of N, S, or O;
and
R26, at each occurrence, is independently selected from C1-10alkyl, haloC1-10alkyl, C3-10cycloalkyl, C6-10aryl, a 4- to 12-membered heteroaryl or 4- to 12-membered heterocyclyl, wherein the heteroaryl and heterocyclyl consist of carbon atoms and 1, 2, 3, or 4 heteroatoms independently selected from the group consisting of N, S, or O;
provide that:
(i) R1 is not Cl when m is 0, 1 or 2;
R13a-1 is H, —CF3, or methoxy;
R13c-1 is H, OH, methoxy or dimethylamino;
X, Y, Z, R13b-1, R13d-1, R13a-2, R13b-2, R13c-2, R13d-2, R13e-2, R13g-2, R13a-4, R13b-4, R13c-4, R13d-4, R13b-5, R13c-5, R13m-1, R13n-1, R13p-1, and R13q-1 are H;
and
(ii) m is not 0 or 1 when X, Y, R13a, R13d, R13e, R13g, R13a-2, R13b-2, R13c-2, R13d-2, R13a-4, R13b-4, R13c-4, R13d-4 R13b-5, R13c-5, R13h-1 and R13hh-1 are H;
R13b is H or —SO2NH2;
R13c is H, —CONH2, —SO2N(C2H4OH)2, —SO2NHCOCH3, —SO2NH2, -tetrazolyl or (4-aminopiperidinyl)sulfonyl;
R13f is H or —NHC2H4OCH3;
and Z is H, —CO2H, or —CO2CH3.

92 more elements

A compound of formula (Ib) or (Ic):

or an enantiomer, diastereomer, tautomer, or salt thereof wherein:
X is H, F, Cl, Br, I, C1-10 alkoxy, haloC1-10 alkyl, 4- to 12-membered heterocyclyl, —CO2R11 or —NR11R12;
Y is H, F, Cl, Br, I, C1-10 alkoxy, haloC1-10 alkyl, 4- to 12-membered heterocyclyl, —CO2R11 or —NR11R12;
Z is H, Cl, Br, I, C1-10 alkoxy, haloC1-10 alkyl, 4- to 12-membered heterocyclyl or —NR11R12;
R11 and R12, at each occurrence, are independently selected from H, C1-10 alkyl, haloC1-10 alkyl, C3-10 cycloalkyl, C6-10aryl, a 4- to 12-membered heteroaryl and a 4- to 12-membered heterocyclyl, wherein the alkyl, cycloalkyl, aryl, heteroaryl and heterocyclyl may be optionally substituted with one or more R13's and the heteroaryl and heterocyclyl consist of carbon atoms and 1, 2, 3, or 4 heteroatoms independently selected from the group consisting of N, S, or O;
R13a is independently H, —OH, F, Cl, Br, I, C1-10 alkyl, C2-10 alkoxy, haloC1-10 alkyl, C3-10 cycloalkyl, C2-12 alkenyl, C6-10aryl, a 4- to 12-membered heteroaryl, a 4- to 12-membered heterocyclyl, a 4- to 12-membered heteroaryl-C1-10 alkyl, —CN, —(CH2)m—SO2R14, —NR14SO2R14, —CONR14R14, —(CH2)m—NR14SO2R14, —(CH2)n—NR14SO2NR14R14, —NR14SO2NR14R14, —CO2NR14R14, —NR14CO2NR14R14, —NR14COR14, —SO2NR14COR14, —SO2NR14CONR14R14, —NR14CO2R14, —CO2R14 or —NR14R14, wherein the alkyl, cycloalkyl, alkenyl, alkoxy, aryl, heteroaryl and heterocyclyl may be optionally substituted with one or more R14a's and the heteroaryl and heterocyclyl consist of carbon atoms and 1, 2, 3, or 4 heteroatoms independently selected from the group consisting of N, S, or O;
R13a-2 is independently H, —OH, F, Br, I, C1-10 alkyl, C1-10 alkoxy, haloC1-10 alkyl, C3-10 cycloalkyl, C2-12 alkenyl, C6-10aryl, a 4- to 12-membered heteroaryl, a 4- to 12-membered heterocyclyl, a 4- to 12-membered heteroaryl-C1-10 alkyl, —(CH2)m—SO2R14, —NR14SO2R14, —CONR14R14, —(CH2)m—SO2NR14R14, —(CH2)m—NR14SO2R14, —(CH2)m—NR14SO2NR14R14, —NR14SO2NR14R14, —CO2NR14R14, —NR14CO2NR14R14, —NR14COR14, —SO2NR14COR14, —SO2NR14CONR14R14, —NR14CO2R14, —CO2R14 or —NR14R14, wherein the alkyl, cycloalkyl, alkenyl, alkoxy, aryl, heteroaryl and heterocyclyl may be optionally substituted with one or more R14a's and the heteroaryl and heterocyclyl consist of carbon atoms and 1, 2, 3, or 4 heteroatoms independently selected from the group consisting of N, S, or O;
R13b is independently H, F, Cl, Br, I, C1-10 alkyl, C1-10 alkoxy, haloC1-10 alkyl, C3-10 cycloalkyl, C2-12 alkenyl, C6-10aryl, a 4- to 12-membered heteroaryl, a 4- to 12-membered heterocyclyl, a 4- to 12-membered heteroaryl-C1-10 alkyl, —CN, —(CH2)m—SO2R14, —NR14SO2R14, —(CH2)m—NR14SO2R14, —(CH2)n—NR14SO2NR14R14, —NR14SO2NR14R14, —CO2NR14R14, —CONR14R14, —NR14CO2NR14R14, —NR14COR14, —SO2NR14COR14, —SO2NR14CONR14R14, —NR14CO2R14, —CO2R14, —NR14R14 or —NR14CONR14R14, wherein the alkyl, cycloalkyl, alkenyl, alkoxy, aryl, heteroaryl and heterocyclyl may be optionally substituted with one or more R14a's and the heteroaryl and heterocyclyl consist of carbon atoms and 1, 2, 3, or 4 heteroatoms independently selected from the group consisting of N, S, or O;
R13b-2 is independently H, —OH, F, Cl, Br, I, C1-10 alkyl, C1-10 alkoxy, haloC1-10 alkyl, C3-10 cycloalkyl, C2-12 alkenyl, C6-10aryl, a 4- to 12-membered heteroaryl, a 4- to 12-membered heterocyclyl, a 4- to 12-membered heteroaryl-C1-10 alkyl, —CN, —(CH2)m—SO2R14, —NR14SO2R14, —(CH2)m—SO2NR14R14, —(CH2)m—NR14SO2R14, —(CH2)n—NR14SO2NR14R14, —NR14SO2NR14R14, —NR14CO2NR14R14;
—NR14COR14, —SO2NR14COR14, —SO2NR14CONR14R14, —NR14CO2R14, —CO2R14 or —NR14R14, wherein the alkyl, cycloalkyl, alkenyl, alkoxy, aryl, heteroaryl and heterocyclyl may be optionally substituted with one or more R14a's and the heteroaryl and heterocyclyl consist of carbon atoms and 1, 2, 3, or 4 heteroatoms independently selected from the group consisting of N, S, or O;
R13c is independently H, —OH, Cl, Br, I, C1-10 alkyl, hydroxyC1-10 alkyl, cyanoC1-10 alkyl, C1-10 alkoxy, haloC1-10 alkyl, C3-10 cycloalkyl, C2-12 alkenyl, C6-10aryl, a 4- to 12-membered heteroaryl, a 4- to 12-membered heterocyclyl, —CN, —(CH2)m—SO2R14, —(CH2)m—OCONR14R14, —NR14SO2R14, —CONR14R14, —(CH2)m—SO2NR14R14, —(CH2)m—NR14SO2R14, —(CH2)m—NR14SO2NR14R14, —NR14SO2NR14R14, —CO2NR14R14, —NR14CO2NR14R14, —NR14COR14, —SO2NR14COR14, —NR14CO2R14, —CO2R26, —NR14R14, —C(═NOR14)NR14R14 or —NR14CONR14R14, wherein the cycloalkyl, alkenyl, alkoxy, aryl, heteroaryl and heterocyclyl may be optionally substituted with one or more R14a's and the heteroaryl and heterocyclyl consist of carbon atoms and 1, 2, or 3 heteroatoms independently selected from the group consisting of N, S, or O;
R13c-2 is independently H, —OH, F, Cl, Br, I, C1-10 alkyl, C1-10 alkoxy, haloC1-10 alkyl, C3-10 cycloalkyl, C2-12 alkenyl, C6-10aryl, a 4- to 12-membered heteroaryl, a 4- to 12-membered heterocyclyl, a 4- to 12-membered heteroaryl-C1-10 alkyl, —CN, —(CH2)m—SO2R14, —NR14SO2R14, —CONR14R14, —(CH2)m—SO2NR14R14, —(CH2)m—NR14SO2R14, —(CH2)n—NR14SO2NR14R14, —NR14SO2NR14R14, —CO2NR14R14, —NR14CO2NR14R14, —NR14COR14, —SO2NR14COR14, —SO2NR14CONR14R14, —NR14CO2R14, —CO2R14 or —NR14R14, wherein the alkyl, cycloalkyl, alkenyl, alkoxy, aryl, heteroaryl and heterocyclyl may be optionally substituted with one or more R14a's and the heteroaryl and heterocyclyl consist of carbon atoms and 1, 2, 3, or 4 heteroatoms independently selected from the group consisting of N, S, or O;
R13d is independently H, —OH, F, Cl, Br, I, C1-10 alkyl, C2-10 alkoxy, haloC1-10 alkyl, C3-10 cycloalkyl, C2-12 alkenyl, C6-10aryl, a 4- to 12-membered heteroaryl, a 4- to 12-membered heterocyclyl, a 4- to 12-membered heteroaryl-C1-10 alkyl, —CN, —(CH2)m—SO2R14, —NR14SO2R14, —CONR14R14, —(CH2)m—NR14SO2R14, —(CH2)n—NR14SO2NR14R14, —NR14SO2NR14R14, —CO2NR14R14, —(CH2)m—SO2NR14R14, —NR14CO2NR14R14, —NR14COR14, —SO2NR14COR14, —SO2NR14CONR14R14, —NR14CO2R14, —CO2R14 or —NR14R14, wherein the alkyl, cycloalkyl, alkenyl, alkoxy, aryl, heteroaryl and heterocyclyl may be optionally substituted with one or more R14a's and the heteroaryl and heterocyclyl consist of carbon atoms and 1, 2, 3, or 4 heteroatoms independently selected from the group consisting of N, S, or O;
R13d-2 is independently H, —OH, Cl, Br, I, C1-10 alkyl, C1-10 alkoxy, haloC1-10 alkyl, C3-10 cycloalkyl, C2-12 alkenyl, C6-10aryl, a 4- to 12-membered heteroaryl, a 4- to 12-membered heterocyclyl, a 4- to 12-membered heteroaryl-C1-10 alkyl, —CN, —(CH2)m—SO2R14, —NR14SO2R14, —CONR14R14, —(CH2)m—SO2NR14R14, —(CH2)m—NR14SO2R14, —(CH2)n—NR14SO2NR14R14, —NR14SO2NR14R14, —CO2NR14R14, —NR14CO2NR14R14, —NR14COR14, —SO2NR14COR14, —SO2NR14CONR14R14, —NR14CO2R14, —CO2R14 or —NR14R14, wherein the alkyl, cycloalkyl, alkenyl, alkoxy, aryl, heteroaryl and heterocyclyl may be optionally substituted with one or more R14a's and the heteroaryl and heterocyclyl consist of carbon atoms and 1, 2, 3, or 4 heteroatoms independently selected from the group consisting of N, S, or O;
R14, at each occurrence, is independently selected from hydrogen, C1-10 alkyl, C3-10 cycloalkyl, C6-10 aryl, a 4- to 12-membered heteroaryl or a 4- to 12-membered heterocyclyl, wherein the alkyl, cycloalkyl, aryl, heteroaryl and heterocyclyl may be optionally substituted with be optionally substituted with 0-3 R14a and the heteroaryl and heterocyclyl consist of carbon atoms and 1, 2, 3, or 4 heteroatoms independently selected from the group consisting of N, S, or O;
R14a, at each occurrence, is independently selected from F, Cl, Br, I, C1-10 alkyl, haloC1-10alkyl, C6-10aryl, C3-10cycloalkyl, a 4- to 12-membered heteroaryl, a 4- to 12-membered heterocyclyl, F, Cl, Br, I, —CN, —CO2H, —CO2R26, —OCONR24R24, —CO2NR24R24, —OCF3, —OR25, —CONR24R24, —SO2R24, —NR24R24 or C6-10arylC1-10alkyl, wherein the heteroaryl and heterocyclyl consist of carbon atoms and 1, 2, 3, or 4 heteroatoms independently selected from the group consisting of N, S, or O;
R24, at each occurrence, is independently selected from hydrogen, C1-10alkyl, C3-10cycloalkyl, C6-10aryl, a 4- to 12-membered heteroaryl or 4- to 12-membered heterocyclyl, wherein the alkyl, aryl, heteroaryl and heterocyclyl may be optionally substituted with one or more R24a's and the heteroaryl and heterocyclyl consist of carbon atoms and 1, 2, 3, or 4 heteroatoms independently selected from the group consisting of N, S, or O;
or
two R24's are taken together with the atoms to which they are attached to form a cyclic ring, wherein the cyclic ring may be optionally substituted with one or more R24a's and optionally contain 1, 2, 3, or 4 heteroatoms independently selected from the group consisting of N, S, or O;
R24a, at each occurrence, is independently selected from F, Cl, Br, I, C1-10 alkyl, haloC1-10alkyl, C6-10aryl, C3-10cycloalkyl, a 4- to 12-membered heteroaryl, a 4- to 12-membered heterocyclyl, —CN, —CO2R25, —OCF3, —OR25, —CONR25R25, —NR25R25 or C6-10arylC1-10alkyl, wherein the heteroaryl and heterocyclyl consist of carbon atoms and 1, 2, 3, or 4 heteroatoms independently selected from the group consisting of N, S, or O;
R25, at each occurrence, is independently selected from hydrogen, C1-10alkyl, C3-10cycloalkyl, C6-10aryl, a 4- to 12-membered heteroaryl or 4- to 12-membered heterocyclyl, wherein the heteroaryl and heterocyclyl consist of carbon atoms and 1, 2, 3, or 4 heteroatoms independently selected from the group consisting of N, S, or O;
and
R26, at each occurrence, is independently selected from C1-10alkyl, haloC1-10alkyl, C3-10cycloalkyl, C6-10aryl, a 4- to 12-membered heteroaryl or 4- to 12-membered heterocyclyl, wherein the heteroaryl and heterocyclyl consist of carbon atoms and 1, 2, 3, or 4 heteroatoms independently selected from the group consisting of N, S, or O;
provided that X, Y, Z, R13a, R13b, R13d, R13a-2, R13b-2, R13c-2 and R13d-2 is not all H when R13c is —C(═O)N(C2H4OCH3)2, —SO2N(C2H4OH)2.

21 more elements

A compound, enantiomer, diastereomer, or salt thereof, selected from

5-Phenyl-N-(pyridin-2-ylmethyl)-2-(pyrimidin-5-yl)quinazolin-4-amine;
5-Phenyl-N-(pyridin-2-ylmethyl)-2-(trifluoromethyl)quinazolin-4-amine;
2-Cyclopropyl-5-phenyl-N-(pyridin-2-ylmethyl)quinazolin-4-amine;
5-(5-Phenyl-4-(pyridin-2-ylmethylamino)quinazolin-2-yl)nicotinamide;
5-(5-Phenyl-4-(pyridin-2-ylmethylamino)quinazolin-2-yl)pyridine-3-sulfonamide;
5-Phenyl-N-(pyridin-2-ylmethyl)-2-(2H-1,2,3-triazol-4-yl)quinazolin-4-amine;
5-(5-Phenyl-4-(pyridin-2-ylmethylamino)quinazolin-2-yl)pyridin-2(1H)-one;
5-Phenyl-N-(pyridin-2-ylmethyl)-2-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)quinazolin-4-amine;
4-((5-Phenyl-2-(pyrimidin-5-yl)quinazolin-4-ylamino)methyl)benzamide;
2-Chloro-5-phenyl-N-(pyridin-2-yl)quinazolin-4-amine;
2-(2-methoxypyrimidin-5-yl)-5-phenyl-N-(pyridin-2-ylmethyl)quinazolin-4-amine;
Tert-butyl 5-(5-phenyl-4-(pyridin-2-ylmethylamino)quinazolin-2-yl)pyridin-3-ylcarbamate;
245-Aminopyridin-3-yl)-5-phenyl-N-(pyridin-2-ylmethyl)quinazolin-4-amine;
N-(5-(5-phenyl-4-(pyridin-2-ylmethylamino)quinazolin-2-yl)pyridin-3-yl)acetamide;
N-(5-(5-phenyl-4-(pyridin-2-ylmethylamino)quinazolin-2-yl)pyridin-3-yl)sulfamide;
1-(5-(5-Phenyl-4-(pyridin-2-ylmethylamino)quinazolin-2-yl)pyridin-3-yl)urea;
2-(2-Aminopyrimidin-5-yl)-5-phenyl-N-(pyridin-2-ylmethyl)quinazolin-4-amine;
5-(5-Phenyl-4-(pyridin-2-ylmethylamino)quinazolin-2-yl)pyrimidine-2-carbonitrile;
5-(5-Phenyl-4-(pyridin-2-ylmethylamino)quinazolin-2-yl)pyrimidine-2-carboxamide;
1-Methyl-2-oxo-5-(5-phenyl-4-(pyridin-2-ylmethylamino)quinazolin-2-yl)-1,2-dihydropyridine-3-sulfonamide;
2-Amino-5-(5-phenyl-4-(pyridin-2-ylmethylamino)quinazolin-2-yl)pyridine-3-sulfonamide;
N-(5-(5-phenyl-4-(pyridin-2-ylmethylamino)quinazolin-2-yl)pyridin-3-yl)methane sulfonamide;
N-(2-methoxyethyl)-5-(5-phenyl-4-(pyridin-2-ylmethylamino)quinazolin-2-yl)pyridine-3-sulfonamide;
Ethyl 2-(5-(5-phenyl-4-(pyridin-2-ylmethylamino)quinazolin-2-yl)pyridine-3-sulfonamido)acetate;
2-Methoxy-5-(5-phenyl-4-(pyridin-2-ylmethylamino)quinazolin-2-yl)pyridine-3-sulfonamide;
N-(2-amino-2-oxoethyl)-5-(5-phenyl-4-(pyridin-2-ylmethylamino)quinazolin-2-yl)nicotinamide;
2-(5-(5-Phenyl-4-(pyridin-2-ylmethylamino)quinazolin-2-yl)pyridine-3-sulfonamido)acetamide;
2-Methyl-6-(5-phenyl-4-(86yridine-2-ylmethylamino)quinazolin-2-yl)imidazo[1,2-a]pyridine-8-sulfonamide;
(5-(5-Phenyl-4-(pyridin-2-ylmethylamino)quinazolin-2-yl)pyridin-3-yl)methanol;
2-(5-(5-Phenyl-4-(pyridin-2-ylmethylamino)quinazolin-2-yl)pyridin-3-yl)propane-1,3-diol;
6-(5-phenyl-4-(pyridin-2-ylmethylamino)quinazolin-2-yl)pyrazine-2-sulfonamide;
2-(5-(3,5-Dimethylisoxazol-4-yl)pyridin-3-yl)-5-phenyl-N-(pyridin-2-ylmethyl)quinazolin-4-amine;
6-(5-Phenyl-4-(pyridin-2-ylmethylamino)quinazolin-2-yl)-1H-imidazo[4,5-b]pyridin-2(3H)-one;
2-(5-(5-Phenyl-4-(pyridin-2-ylmethylamino)quinazolin-2-yl)pyridin-3-yl)acetonitrile;
2-(5-(1,2,4-Oxadiazol-3-yl)pyridin-3-yl)-5-phenyl-N-(pyridin-2-ylmethyl)quinazolin-4-amine;
2-(5-(5-Phenyl-4-(pyridin-2-ylmethylamino)quinazolin-2-yl)pyridin-3-yl)acetamide;
2-(5-(1,3,4-Oxadiazol-2-yl)pyridin-3-yl)-5-phenyl-N-(pyridin-2-ylmethyl)quinazolin-4-amine;
2-((5-(Oxazol-5-yl)pyridin-3-yl)-5-phenyl-N-(pyridin-2-ylmethyl)quinazolin-4-amine;
Methyl 3-(5-(5-phenyl-4-(pyridin-2-ylmethylamino)quinazolin-2-yl)pyridin-3-yl)-1,2,4-oxadiazole-5-carboxylate;
3-(5-(5-Phenyl-4-(pyridin-2-ylmethylamino)quinazolin-2-yl)pyridin-3-yl)-1,2,4-oxadiazole-5-carboxamide;
2-(5-(4H-1,2,4-triazol-4-yl)pyridin-3-yl)-5-phenyl-N-(pyridin-2-ylmethyl)quinazolin-4-amine;
Methyl 3-(5-(5-phenyl-4-(pyridin-2-ylmethylamino)quinazolin-2-yl)pyridin-3-yl)propanoate;
(E)-methyl 3-(5-(5-phenyl-4-(pyridin-2-ylmethylamino)quinazolin-2-yl)pyridin-3-yl)acrylate;
3-(5-(5-Phenyl-4-(pyridin-2-ylmethylamino)quinazolin-2-yl)pyridin-3-yl)propanamide;
Methyl 3-(5-phenyl-4-(pyridin-2-ylmethylamino)quinazolin-2-yl)propanoate;
5-(5-(5-Phenyl-4-(pyridin-2-ylmethylamino)quinazolin-2-yl)pyridin-3-yl)-1,3,4-oxadiazole-2-carboxamide;
2-(5-(5-Phenyl-4-(pyridin-2-ylmethylamino)quinazolin-2-yl)pyridin-3-yl)propan-2-ol;
(5-(5-Phenyl-4-(pyridin-2-ylmethylamino)quinazolin-2-yl)pyridin-3-yl)methyl isopropylcarbamate;
2-Methyl-1-(5-(5-phenyl-4-(pyridin-2-ylmethylamino)quinazolin-2-yl)pyridin-3-yl)propan-1-ol;
2-(5-(5-Phenyl-4-(pyridin-2-ylmethylamino)quinazolin-2-yl)pyridin-3-ylsulfonyl)acetamide;
2-Methyl-2-(5-(5-phenyl-4-(pyridin-2-ylmethylamino)quinazolin-2-yl)pyridin-3-yl)propanenitrile;
2-(5-(5-Phenyl-4-(pyridin-2-ylmethylamino)quinazolin-2-yl)pyridin-3-yl)propanamide;
Methyl 5-(5-(5-phenyl-4-(pyridin-2-ylmethylamino)quinazolin-2-yl)pyridin-3-yl)-1,3,4-oxadiazole-2-carboxylate;
1-(5-(5-Phenyl-4-(pyridin-2-ylmethylamino)quinazolin-2-yl)pyridin-3-yl)ethanol;
4-(5-Phenyl-4-(pyridin-2-ylmethylamino)quinazolin-2-yl)thiazol-2-amine;
(4-Aminopiperidin-1-yl)(3-(5-(5-phenyl-4-(pyridin-2-ylmethylamino)quinazolin-2-yl)pyridin-3-yl)-1,2,4-oxadiazol-5-yl)methanone;
1-(5-(5-Phenyl-4-(pyridin-2-ylmethylamino)quinazolin-2-yl)pyridin-3-yl)cyclopropanecarbonitrile;
2-(5-(5-Phenyl-4-(pyridin-2-ylmethylamino)quinazolin-2-yl)pyridin-3-yl)ethanesulfonamide;
1-(5-Phenyl-4-(pyridin-2-ylmethylamino)quinazolin-2-yl)cyclopropanecarbonitrile;
N-((5-(5-phenyl-4-(pyridin-2-ylmethylamino)quinazolin-2-yl)pyridin-3-yl)methyl)methanesulfonamide;
Ethyl 5-(5-phenyl-4-(pyridin-2-ylmethylamino)quinazolin-2-yl)isoxazole-3-carboxylate;
Ethyl 4-(5-phenyl-4-(pyridin-2-ylmethylamino)quinazolin-2-yl)thiazole-2-carboxylate;
Tert-butyl 4-(5-phenyl-4-(pyridin-2-ylmethylamino)quinazolin-2-yl)piperidine-1-carboxylate;
(Z)-methyl 2-amino-3-(5-phenyl-4-(pyridin-2-ylmethylamino)quinazolin-2-yl)acrylate;
5-(5-(5-Phenyl-4-(pyridin-2-ylmethylamino)quinazolin-2-yl)pyridin-3-yl)-1,3,4-oxadiazol-2-amine;
4-(5-Phenyl-4-(pyridin-2-ylmethylamino)quinazolin-2-yl)thiazole-2-carboxamide;
1-(5-(5-Phenyl-4-(pyridin-2-ylmethylamino)quinazolin-2-yl)-4,5-dihydroisoxazol-3-yl)butan-1-one;
4-(5-Phenyl-4-(pyridin-2-ylmethylamino)quinazolin-2-yl)but-3-yn-1-ol;
2-((5-(5-Phenyl-4-(pyridin-2-ylmethylamino)quinazolin-2-yl)pyridin-3-yl)methylsulfonyl)acetamide;
5-Phenyl-N-(pyridin-2-ylmethyl)-2-(2,2,5-trimethyl-1,3-dioxan-5-yl)quinazolin-4-amine;
2-Methyl-2-(5-phenyl-4-(pyridin-2-ylmethylamino)quinazolin-2-yl)propane-1,3-diol;
3-(5-Phenyl-4-(pyridin-2-ylmethylamino)quinazolin-2-yl)isoxazole-5-carboxamide;
N-((1-(5-phenyl-4-(pyridin-2-ylmethylamino)quinazolin-2-yl)cyclopropyl)methyl)methanesulfonamide;
N-((1-(5-phenyl-4-(pyridin-2-ylmethylamino)quinazolin-2-yl)cyclopropyl)methyl)sulfamide;
4-(5-Phenyl-4-(pyridin-2-ylmethylamino)quinazolin-2-yl)piperidine-1-sulfonamide;
5-(5-Phenyl-4-(pyridin-2-ylmethylamino)quinazolin-2-yl)isoxazole-3-carboxamide;
4-(5-Phenyl-4-(pyridin-2-ylmethylamino)quinazolin-2-yl)thiazole-2-sulfonamide;
4-(5-Phenyl-4-(pyridin-2-ylmethylamino)quinazolin-2-yl)thiazole-2-sulfonamide.

75 more elements

Dependencies are inferred from the claim text.

Facts

Application: 13/393,328Filed 1 Sep 2010
Priority: 3 Sep 2009
Published: 13 Sep 2012
Term ends: Not estimatedThe source records don’t support an estimate.

Classification29 codes

C07D 401/14
Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a…:…
A61K 31/517
Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim: ortho- or peri-condensed with carbocyclic ring systems, e.g. quinazoline, perimidine
A61K 31/5377
1,4-Oxazines, e.g. morpholine: not condensed and containing further heterocyclic rings, e.g. timolol
A61K 31/549
Having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame: having two or more nitrogen atoms in…

Family

Application61/239,452Us provisional application · filed 3 Sep 2009
US 8,575,184 B2Related patent
US 2012/0232068 A1This patent

From the US filing history. Foreign family members aren’t listed.

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Abstract

A compound of formula I

or an enantiomer, diastereomer, tautomer, or salt thereof wherein:
X is H, —OH, F, Cl, Br, I, C1-10 alkyl, C1-10 alkoxy, haloC1-10 alkyl, C2-12 alkenyl, C2-12 alkynyl, C3-10 cycloalkyl, a 4- to 12-membered heteroaryl, 4- to 12-membered heterocyclyl, —CN, —NO2, —NR11SO2R12, —SO2NR11R12, —CONR11R12, —NR11CONR11R12, —NCOR11, —NR11SO2NR11R12, —OCONR11R12, —CO2R11 or —NR11R12;
Y is H, F, Cl, Br, I, C1-10 alkyl, C1-10 alkoxy, haloC1-10 alkyl, C2-12 alkenyl, C2-12 alkynyl, C3-10 cycloalkyl, a 4- to 12-membered heteroaryl, 4- to 12-membered heterocyclyl, —CN, —NO2, —SO2NR11R12, —CONR11R12, —NR11CONR11R12, —NCOR11, —NR11SO2NR11R12, —OCONR11R12, —CO2R11 or —NR11R12;
Z is H, Cl, Br, I, C1-10 alkyl, C1-10 alkoxy, haloC1-10 alkyl, C2-12 alkenyl, C2-12 alkynyl, C3-10 cycloalkyl, a 6- to 12-membered heteroaryl, 4- to 12-membered heterocyclyl, —NO2, —NR11SO2R12, —SO2NR11R12, —NR11CONR11R12, —NCOR11, —NR11SO2NR11R12, —OCONR11R12, —CO2R11 or —NR11R12;
A is —(CH2)m—R2, —CH(R25)(R26), —CH(R26)—CO2—R2a or —(CH2)n-1—NR25—CO2—R24;
m is 0 to 4;
n is 1 to 4;
n-1 is 2 to 4;
R1 is —OH, F, Cl, Br, I, C1-10 alkyl, haloC1-10 alkyl, C2-12 alkenyl, C3-10 cycloalkyl, —CN, —(CH2)m—SO2NR11R12, —(CH2)m—CO2R11 or —(CH2)n—NR11SO2R12, wherein the alkenyl and cycloalkyl may be optionally substituted with one or more RD's;
or
R1 is selected from the group consisting of:
Or
R1 is
R2 is C1-10 alkyl, cyclopropyl optionally substituted with one or more R13′5;
C4-10 cycloalkyl optionally substituted with one or more R13bb's;
C3-10 cycloalkenyl optionally substituted with one or more R13b's;
or —NR14R14;
provided that R2 is not —NR14R14 when m is 0, 1 or 3;
or
R2 is
or
R2 is selected from the group consisting of:
R2a is C1-10 alkyl, C3-10 cycloalkyl, C6-10 aryl, —NR14R14, a 4- to 12-membered heteroaryl or 4- to 12-membered heterocyclyl, any of which is optionally substituted with one or more R13's and the heteroaryl and heterocyclyl consist of carbon atoms and 1, 2, 3, or 4 heteroatoms independently selected from the group consisting of N, S, or O;
R11 and R12, at each occurrence, are independently selected from H, C1-10 alkyl, haloC1-10 alkyl, C3-10 cycloalkyl, C6-10aryl, a 4- to 12-membered heteroaryl and a 4- to 12-membered heterocyclyl, wherein the alkyl, cycloalkyl, aryl, heteroaryl and heterocyclyl may be optionally substituted with one or more R13's and the heteroaryl and heterocyclyl consist of carbon atoms and 1, 2, 3, or 4 heteroatoms independently selected from the group consisting of N, S, or O;
or
R11 and R12 are taken together with the nitrogen to which they are attached to form a 4- to 12-membered heterocyclyl, wherein the heterocyclyl may be optionally substituted with one or more R13's and the heterocyclyl consists of carbon atoms and 1, 2, 3, or 4 heteroatoms independently selected from the group consisting of N, S, or O;
R13, at each occurrence, is independently H, —OH, F, Cl, Br, I, C1-10 alkyl, C1-10 alkoxy, haloC1-10 alkyl, C3-10 cycloalkyl, C2-12 alkenyl, C2-12 alkynyl, C6-10aryl, a 4- to 12-membered heteroaryl, a 4- to 12-membered heterocyclyl, a 4- to 12-membered heteroaryl-C1-10 alkyl, —CN, —NO2, —(CH2)m—SO2R14, —NR14SO2R14, —O, —CONR14R14, —(CH2)m—SO2NR14R14, —(CH2)m—NR14SO2R14, —(CH2)m—NR14SO2NR14R14, —NR14SO2NR14R14, —CO2NR14R14, —NR14CO2NR14R14, —NR14COR14, —SO2NR14COR14, —SO2NR14CONR14R14, —NR14CO2R14, —CO2R14, —NR14R14, —NR14CONR14R14, —C(═NOR14)NR14R14, —CONR14OR14 or —NCOR14, wherein the alkyl, cycloalkyl, alkenyl, alkoxy, aryl, heteroaryl and heterocyclyl may be optionally substituted with one or more R14a's and the heteroaryl and heterocyclyl consist of carbon atoms and 1, 2, 3, or 4 heteroatoms independently selected from the group consisting of N, S, or O;
provided that when R13 is alkyl substituted with one R14a, R14a is not —OH;
R13a, at each occurrence, is independently H, —OH, F, Cl, Br, I, C2-10 alkyl, C1-10 alkoxy, haloC1-10 alkyl, C3-10 cycloalkyl, C2-12 alkenyl, C2-12 alkynyl, C6-10aryl, a 4- to 12-membered heteroaryl, a 4- to 12-membered heterocyclyl, a 4- to 12-membered heteroaryl-C1-10 alkyl, —CN, —NO2, —(CH2)m—SO2R14, —NR14SO2R14, ═O, —CONR14R14, —(CH2)m—NR14SO2R14, —(CH2)m—NR14SO2NR14R14, —NR14SO2NR14R14, —CO2NR14R14, —NR14CO2NR14R14, —NR14COR14, —SO2NR14COR14, —SO2NR14CONR14R14, —NR14CO2R14, —CO2R14, —NR14R14, —NR14CONR14R14, —C(═NOR14)NR14R14, —CONR14OR14 or —NCOR14, wherein the alkyl, cycloalkyl, alkenyl, alkoxy, aryl, heteroaryl and heterocyclyl may be optionally substituted with one or more R14a's and the heteroaryl and heterocyclyl consist of carbon atoms and 1, 2, 3, or 4 heteroatoms independently selected from the group consisting of N, S, or O;
R13aa, at each occurrence, is independently H, —OH, F, Cl, Br, I, C1-10 alkyl, C1-10 alkoxy, haloC1-10 alkyl, C3-10 cycloalkyl, C2-12 alkenyl, C2-12 alkynyl, C6-10aryl, a 4- to 12-membered heteroaryl, a 4- to 12-membered heterocyclyl, a 4- to 12-membered heteroaryl-C1-10 alkyl, —CN, —NO2, —(CH2)m—SO2R14, —NR14SO2R14, —O, —CONR14R14, —(CH2)m—SO2NR14R14, —(CH2)m—NR14SO2R14, —(CH2)m—NR14SO2NR14R14, —NR14SO2NR14R14, —CO2NR14R14, —NR14CO2NR14R14, —NR14COR14, —SO2NR14COR14, —SO2NR14CONR14R14, —NR14CO2R14, —CO2R14, —NR14R14, —NR14CONR14R14, —C(═NOR14)NR14R14, —CONR14OR14 or —NCOR14, wherein the alkyl, cycloalkyl, alkenyl, alkoxy, aryl, heteroaryl and heterocyclyl may be optionally substituted with one or more R14a's and the heteroaryl and heterocyclyl consist of carbon atoms and 1, 2, 3, or 4 heteroatoms independently selected from the group consisting of N, S, or O;
R13a-1, at each occurrence, is independently H, —OH, F, Cl, Br, I, C1-10 alkyl, C1-10 alkoxy, haloC1-10 alkyl, C3-10 cycloalkyl, C2-12 alkenyl, C2-12 alkynyl, C6-10aryl, a 4- to 12-membered heteroaryl, a 4- to 12-membered heterocyclyl, a 4- to 12-membered heteroaryl-C1-10 alkyl, —CN, —NO2, —(CH2)m—SO2R14, —NR14SO2R14, ═O, —CONR14R14, —(CH2)m—SO2NR14R14, —(CH2)m—NR14SO2R14, —(CH2)m—NR14SO2NR14R14, —NR14SO2NR14R14, —CO2NR14R14, —NR14CO2NR14R14, —NR14COR14, —SO2NR14COR14, —SO2NR14CONR14R14, —NR14CO2R14, —CO2R14, —NR14R14, —NR14CONR14R14, —C(═NOR14)NR14R14, —CONR14OR14 or —NCOR14, wherein the alkyl, cycloalkyl, alkenyl, alkoxy, aryl, heteroaryl and heterocyclyl may be optionally substituted with one or more R14a's and the heteroaryl and heterocyclyl consist of carbon atoms and 1, 2, 3, or 4 heteroatoms independently selected from the group consisting of N, S, or O;
R13a-2, at each occurrence, is independently H, —OH, F, Br, I, C1-10 alkyl, C1-10 alkoxy, haloC1-10 alkyl, C3-10 cycloalkyl, C2-12 alkenyl, C2-12 alkynyl, C6-10aryl, a 4- to 12-membered heteroaryl, a 4- to 12-membered heterocyclyl, a 4- to 12-membered heteroaryl-C1-10 alkyl, —CN, —NO2, —(CH2)m—SO2R14, —NR14SO2R14, ═O, —CONR14R14, —(CH2)m—SO2NR14R14, —(CH2)m—NR14SO2R14, —(CH2)m—NR14SO2NR14R14, —NR14SO2NR14R14, —CO2NR14R14, —NR14CO2NR14R14, —NR14COR14, —SO2NR14COR14, —SO2NR14CONR14R14, —NR14CO2R14, —CO2R14, —NR14R14, —NR14CONR14R14, —C(═NOR14)NR14R14, —CONR14OR14 or —NCOR14, wherein the alkyl, cycloalkyl, alkenyl, alkoxy, aryl, heteroaryl and heterocyclyl may be optionally substituted with one or more R14a's and the heteroaryl and heterocyclyl consist of carbon atoms and 1, 2, 3, or 4 heteroatoms independently selected from the group consisting of N, S, or O;
R13a-4, at each occurrence, is independently H, —OH, F, Cl, Br, I, C1-10 alkyl, C1-10 alkoxy, haloC1-10 alkyl, C3-10 cycloalkyl, C2-12 alkenyl, C2-12 alkynyl, C6-10aryl, a 4- to 12-membered heteroaryl, a 4- to 12-membered heterocyclyl, a 4- to 12-membered heteroaryl-C1-10 alkyl, —CN, —NO2, —(CH2)m—SO2R14, —NR14SO2R14, ═O, —CONR14R14, —(CH2)m—SO2NR14R14, —(CH2)m—NR14SO2R14, —(CH2)m—NR14SO2NR14R14, —NR14SO2NR14R14, —CO2NR14R14, —NR14CO2NR14R14, —NR14COR14, —SO2NR14COR14, —SO2NR14CONR14R14, —NR14CO2R14, —CO2R14, —NR14R14, —NR14CONR14R14, —C(═NOR14)NR14R14, —CONR14OR14 or —NCOR14, wherein the alkyl, cycloalkyl, alkenyl, alkoxy, aryl, heteroaryl and heterocyclyl may be optionally substituted with one or more R14a's and the heteroaryl and heterocyclyl consist of carbon atoms and 1, 2, 3, or 4 heteroatoms independently selected from the group consisting of N, S, or O;
R13b, at each occurrence, is independently H, F, Cl, Br, I, C1-10 alkyl, C1-10 alkoxy, haloC1-10 alkyl, C3-10 cycloalkyl, C2-12 alkenyl, C2-12 alkynyl, C6-10aryl, a 4- to 12-membered heteroaryl, a 4- to 12-membered heterocyclyl, a 4- to 12-membered heteroaryl-C1-10 alkyl, —CN, —NO2, —(CH2)m—SO2R14, —NR14SO2R14, ═O, —(CH2)m—SO2NR14R14, —(CH2)m—NR14SO2R14, —(CH2)m—NR14SO2NR14R14, —NR14SO2NR14R14, —CO2NR14R14, —NR14CO2NR14R14, —NR14COR14, —SO2NR14COR14, —SO2NR14CONR14R14, —NR14CO2R14, —CO2R14, —NR14R14, —NR14CONR14R14, —C(═NOR14)NR14R14, —CONR14OR14 or —NCOR14, wherein the alkyl, cycloalkyl, alkenyl, alkoxy, aryl, heteroaryl and heterocyclyl may be optionally substituted with one or more R14a's and the heteroaryl and heterocyclyl consist of carbon atoms and 1, 2, 3, or 4 heteroatoms independently selected from the group consisting of N, S, or O;
R13bb, at each occurrence, is independently H, F, Cl, Br, I, C1-10 alkyl, C1-10 alkoxy, haloC1-10 alkyl, C3-10 cycloalkyl, C2-12 alkenyl, C2-12 alkynyl, C6-10aryl, a 4- to 12-membered heteroaryl, a 4- to 12-membered heterocyclyl, a 4- to 12-membered heteroaryl-C1-10 alkyl, —CN, —NO2, —(CH2)m—SO2R14, —NR14SO2R14, ═O, —(CH2)m—SO2NR14R14, —(CH2)m—NR14SO2R14, —(CH2)m—NR14SO2NR14R14, —NR14SO2NR14R14, —CO2NR14R14, —NR14CO2NR14R14, —NR14COR14, —SO2NR14COR14, —SO2NR14CONR14R14, —NR14CO2R14, —CO2R14, —NR14R14, —NR14CONR14R14, —C(═NOR14)NR14R14, —CONR14OR14 or —NCOR14, wherein the alkyl, cycloalkyl, alkenyl, alkoxy, aryl, heteroaryl and heterocyclyl may be optionally substituted with one or more R14a's and the heteroaryl and heterocyclyl consist of carbon atoms and 1, 2, 3, or 4 heteroatoms independently selected from the group consisting of N, S, or O;
R13b-1, at each occurrence, is independently H, —OH, F, Cl, Br, I, C1-10 alkyl, C1-10 alkoxy, haloC1-10 alkyl, C3-10 cycloalkyl, C2-12 alkenyl, C2-12 alkynyl, C6-10aryl, a 4- to 12-membered heteroaryl, a 4- to 12-membered heterocyclyl, a 4- to 12-membered heteroaryl-C1-10 alkyl, —CN, —NO2, —(CH2)m—SO2R14, —NR14SO2R14, —O, —CONR14R14, —(CH2)m—SO2NR14R14, —(CH2)m—NR14SO2R14, —(CH2)m—NR14SO2NR14R14, —NR14SO2NR14R14, —CO2NR14R14, —NR14CO2NR14R14, —NR14COR14, —SO2NR14COR14, —SO2NR14CONR14R14, —NR14CO2R14, —CO2R14, —NR14R14, —NR14CONR14R14, —C(═NOR14)NR14R14, —CONR14OR14 or —NCOR14, wherein the alkyl, cycloalkyl, alkenyl, aryl, heteroaryl and heterocyclyl may be optionally substituted with one or more R14a's and the heteroaryl and heterocyclyl consist of carbon atoms and 1, 2, 3, or 4 heteroatoms independently selected from the group consisting of N, S, or O;
R13b-2, at each occurrence, is independently H, —OH, Cl, Br, I, C1-10 alkyl, C1-10 alkoxy, haloC2-10 alkyl, C3-10 cycloalkyl, C2-12 alkenyl, C2-12 alkynyl, C6-10aryl, a 4- to 12-membered heteroaryl, a 4- to 12-membered heterocyclyl, a 4- to 12-membered heteroaryl-C1-10 alkyl, —CN, —NO2, —(CH2)m—SO2R14, —NR14SO2R14, —O, —(CH2)m—SO2NR14R14, —(CH2)m—NR14SO2R14, —(CH2)m—NR14SO2NR14R14, —NR14SO2NR14R14, —CO2NR14R14, —NR14CO2NR14R14, —NR14COR14, —SO2NR14COR14, —SO2NR14CONR14R14, —NR14CO2R14, —CO2R14, —NR14R14, —NR14CONR14R14, —C(═NOR14)NR14R14, —CONR14OR14 or —NCOR14, wherein the alkyl, cycloalkyl, alkenyl, alkoxy, aryl, heteroaryl and heterocyclyl may be optionally substituted with one or more R14a's and the heteroaryl and heterocyclyl consist of carbon atoms and 1, 2, 3, or 4 heteroatoms independently selected from the group consisting of N, S, or O;
R13b-4, at each occurrence, is independently H, —OH, F, Cl, Br, I, C1-10 alkyl, C1-10 alkoxy, haloC1-10 alkyl, C3-10 cycloalkyl, C2-12 alkenyl, C2-12 alkynyl, C6-10aryl, a 4- to 12-membered heteroaryl, a 4- to 12-membered heterocyclyl, a 4- to 12-membered heteroaryl-C1-10 alkyl, —CN, —NO2, —(CH2)m—SO2R14, —NR14SO2R14, ═O, —CONR14R14, —(CH2)m—SO2NR14R14, —(CH2)m—NR14SO2R14, —NR14SO2NR14R14, —CO2NR14R14, —NR14CO2NR14R14, —SO2NR14COR14, —SO2NR14CONR14R14, —NR14CO2R14, —CO2R14, —NR14R14, —NR14CONR14R14, —C(═NOR14)NR14R14, —CONR14OR14 or —NCOR14, wherein the alkyl, cycloalkyl, alkenyl, alkoxy, aryl, heteroaryl and heterocyclyl may be optionally substituted with one or more R14a's and the heteroaryl and heterocyclyl consist of carbon atoms and 1, 2, 3, or 4 heteroatoms independently selected from the group consisting of N, S, or O;
R13b-5, at each occurrence, is independently H, —OH, F, Cl, Br, I, C1-10 alkyl, C1-10 alkoxy, haloC1-10 alkyl, C3-10 cycloalkyl, C2-12 alkenyl, C2-12 alkynyl, C6-10aryl, a 4- to 12-membered heteroaryl, a 4- to 12-membered heterocyclyl, a 4- to 12-membered heteroaryl-C1-10 alkyl, —CN, —NO2, —(CH2)m—SO2R14, —NR14SO2R14, ═O, —CONR14R14, —(CH2)m—SO2NR14R14, —(CH2)m—NR14SO2R14, —(CH2)m—NR14SO2NR14R14, —NR14SO2NR14R14, —CO2NR14R14, —NR14CO2NR14R14, —NR14COR14, —SO2NR14COR14, —SO2NR14CONR14R14, —NR14CO2R14, —CO2R14, —NR14R14, —NR14CONR14R14, —C(═NOR14)NR14R14, —CONR14OR14 or —NCOR14, wherein the alkyl, cycloalkyl, alkenyl, alkoxy, aryl, heteroaryl and heterocyclyl may be optionally substituted with one or more R14a's and the heteroaryl and heterocyclyl consist of carbon atoms and 1, 2, 3, or 4 heteroatoms independently selected from the group consisting of N, S, or O;
R13c, at each occurrence, is independently H, —OH, F, Cl, Br, I, C1-10 alkyl, C1-10 alkoxy, haloC1-10 alkyl, C3-10 cycloalkyl, C2-12 alkenyl, C2-12 alkynyl, C6-10aryl, a 4- to 12-membered heteroaryl, a 4- to 12-membered heterocyclyl, —CN, —NO2, —(CH2)m—SO2R14, —NR14SO2R14, ═O, —CONR14R14, —(CH2)m—SO2NR14R14, —(CH2)m—NR14SO2R14, —(CH2)m—NR14SO2NR14R14, —NR14SO2NR14R14, —(CH2)m—OCONR14R14, —CO2NR14R14, —NR14CO2NR14R14, —NR14COR14, —SO2NR14COR14, —NR14CO2R14, —CO2R26, —NR14R14, —NR14CONR14R14, —C(═NOR14)NR14R14, —CONR14OR14 or —NCOR14, wherein the alkyl, cycloalkyl, alkenyl, alkoxy, aryl, heteroaryl and heterocyclyl may be optionally substituted with one or more R14a's and the heteroaryl and heterocyclyl consist of carbon atoms and 1, 2, 3, or 4 heteroatoms independently selected from the group consisting of N, S, or O;
R13cc, at each occurrence, is independently H, F, Cl, Br, I, C1-10 alkyl, C1-10 alkoxy, haloC1-10 alkyl, C3-10 cycloalkyl, C2-12 alkenyl, C2-12 alkynyl, C6-10aryl, a 4- to 12-membered heteroaryl, a 4- to 12-membered heterocyclyl, a 4- to 12-membered heteroaryl-C1-10 alkyl, —CN, —NO2, —(CH2)m—SO2R14, —NR14SO2R14, ═O, —CONR14R14, —(CH2)m—SO2NR14R14, —(CH2)m—NR14SO2R14, —(CH2)m—NR14SO2NR14R14, —NR14SO2NR14R14, —CO2NR14R14, —NR14CO2NR14R14, —NR14COR14, —SO2NR14COR14, —SO2NR14CONR14R14, —NR14CO2R14, —CO2R14, —NR14R14, —NR14CONR14R14, —C(═NOR14)NR14R14, —CONR14OR14, or —NCOR14, wherein the alkyl, cycloalkyl, alkenyl, alkoxy, aryl, heteroaryl and heterocyclyl may be optionally substituted with one or more R14a's and the heteroaryl and heterocyclyl consist of carbon atoms and 1, 2, 3, or 4 heteroatoms independently selected from the group consisting of N, S, or O;
R13c-1, at each occurrence, is independently H, —OH, F, Cl, Br, I, C1-10 alkyl, C1-10 alkoxy, haloC2-10 alkyl, C3-10 cycloalkyl, C2-12 alkenyl, C2-12 alkynyl, C6-10aryl, a 6- to 12-membered heteroaryl, a 6- to 12-membered heterocyclyl, a 4- to 12-membered heteroaryl-C1-10 alkyl, —NO2, —NR14SO2R14, ═O, —(CH2)m—NR14SO2R14, —NR14SO2NR14R14, —CO2NR14R14, —NR14CO2NR14R14, —NR14COR14, —SO2NR14COR14, —SO2NR14CONR14R14, —NR14CO2R14, —NR14R14, —C(═NOR14)NR14R14, —CONR14OR14 or —NCOR14, wherein the alkyl, cycloalkyl, alkenyl, aryl, heteroaryl and heterocyclyl may be optionally substituted with one or more R14a's and the heteroaryl and heterocyclyl consist of carbon atoms and 1, 2, 3, or 4 heteroatoms independently selected from the group consisting of N, S, or O;
R13c-2, at each occurrence, is independently H, —OH, F, Cl, Br, I, C2-10 alkyl, C1-10 alkoxy, haloC1-10 alkyl, C3-10 cycloalkyl, C2-12 alkenyl, C2-12 alkynyl, C6-10aryl, a 4- to 12-membered heteroaryl, a 4- to 12-membered heterocyclyl, a 4- to 12-membered heteroaryl-C1-10 alkyl, —CN, —NO2, —(CH2)m—SO2R14, —NR14SO2R14, ═O, —CONR14R14, —(CH2)m—SO2NR14R14, —(CH2)m—NR14SO2R14, —(CH2)m—NR14SO2NR14R14, —NR14SO2NR14R14, —CO2NR14R14, —NR14CO2NR14R14, —NR14COR14, —SO2NR14COR14, —SO2NR14CONR14R14, —NR14CO2R14, —CO2R14, —NR14R14, —NR14CONR14R14, —C(═NOR14)NR14R14, —CONR14OR14 or —NCOR14, wherein the alkyl, cycloalkyl, alkenyl, alkoxy, aryl, heteroaryl and heterocyclyl may be optionally substituted with one or more R14a's and the heteroaryl and heterocyclyl consist of carbon atoms and 1, 2, 3, or 4 heteroatoms independently selected from the group consisting of N, S, or O;
R13c-4, at each occurrence, is independently H, —OH, Cl, Br, I, C1-10 alkyl, C1-10 alkoxy, haloC1-10 alkyl, C3-10 cycloalkyl, C2-12 alkenyl, C2-12 alkynyl, C6-10aryl, a 4- to 12-membered heteroaryl, a 4- to 12-membered heterocyclyl, a 4- to 12-membered heteroaryl-C1-10 alkyl, —CN, —NO2, —(CH2)m—SO2R14, —NR14SO2R14, ═O, —CONR14R14, —(CH2)m—SO2NR14R14, —(CH2)m—NR14SO2R14, —(CH2)m—NR14SO2NR14R14, —NR14SO2NR14R14, —CO2NR14R14, —NR14CO2NR14R14, —NR14COR14, —SO2NR14COR14, —SO2NR14CONR14R14, —NR14CO2R14, —CO2R14, —NR14R14, —NR14CONR14R14, —C(═NOR14)NR14R14, —CONR14OR14 or —NCOR14, wherein the alkyl, cycloalkyl, alkenyl, alkoxy, aryl, heteroaryl and heterocyclyl may be optionally substituted with one or more R14a's and the heteroaryl and heterocyclyl consist of carbon atoms and 1, 2, 3, or 4 heteroatoms independently selected from the group consisting of N, S, or O;
R13c-5, at each occurrence, is independently H, —OH, F, Cl, Br, I, C1-10 alkyl, C1-10 alkoxy, haloC1-10 alkyl, C3-10 cycloalkyl, C2-12 alkenyl, C2-12 alkynyl, C6-10aryl, a 4- to 12-membered heteroaryl, a 4- to 12-membered heterocyclyl, a 4- to 12-membered heteroaryl-C1-10 alkyl, —CN, —NO2, —(CH2)m—SO2R14, —NR14SO2R14, ═O, —CONR14R14, —(CH2)m—SO2NR14R14, —(CH2)m—NR14SO2R14, —(CH2)m—NR14SO2NR14R14, —NR14SO2NR14R14, —CO2NR14R14, —NR14CO2NR14R14, —NR14COR14, —SO2NR14COR14, —SO2NR14CONR14R14, —NR14CO2R14, —CO2R14, —NR14R14, —NR14CONR14R14, —C(═NOR14)NR14R14, —CONR14OR14 or —NCOR14, wherein the alkyl, cycloalkyl, alkenyl, alkoxy, aryl, heteroaryl and heterocyclyl may be optionally substituted with one or more R14a's and the heteroaryl and heterocyclyl consist of carbon atoms and 1, 2, 3, or 4 heteroatoms independently selected from the group consisting of N, S, or O;
R13d, at each occurrence, is independently H, —OH, F, Cl, Br, I, C1-10 alkyl, C2-10 alkoxy, haloC1-10 alkyl, C3-10 cycloalkyl, C2-12 alkenyl, C2-12 alkynyl, C6-10aryl, a 4- to 12-membered heteroaryl, a 4- to 12-membered heterocyclyl, a 4- to 12-membered heteroaryl-C1-10 alkyl, —CN, —NO2, —(CH2)m—SO2R14, —NR14SO2R14, —O, —CONR14R14, —(CH2)m—SO2NR14R14, —(CH2)m—NR14SO2R14, —(CH2)m—NR14SO2NR14R14, —NR14SO2NR14R14, —CO2NR14R14, —NR14CO2NR14R14, —NR14COR14, —SO2NR14COR14, —SO2NR14CONR14R14, —NR14CO2R14, —CO2R14, —NR14R14, —NR14CONR14R14, —C(═NOR14)NR14R14, —CONR14OR14 or —NCOR14, wherein the alkyl, cycloalkyl, alkenyl, alkoxy, aryl, heteroaryl and heterocyclyl may be optionally substituted with one or more R14a's and the heteroaryl and heterocyclyl consist of carbon atoms and 1, 2, 3, or 4 heteroatoms independently selected from the group consisting of N, S, or O;
R13dd, at each occurrence, is independently H, —OH, F, Cl, Br, I, C1-10 alkyl, C1-10 alkoxy, haloC1-10 alkyl, C3-10 cycloalkyl, C2-12 alkenyl, C2-12 alkynyl, C6-10aryl, a 4- to 12-membered heteroaryl, a 4- to 12-membered heterocyclyl, a 4- to 12-membered heteroaryl-C1-10 alkyl, —CN, —NO2, —(CH2)m—SO2R14, —NR14SO2R14, ═O, —CONR14R14, —(CH2)m—SO2NR14R14, —(CH2)m—NR14SO2R14, —(CH2)m—NR14SO2NR14R14, —NR14SO2NR14R14, —CO2NR14R14, —NR14CO2NR14R14, —NR14COR14, —SO2NR14COR14, —SO2NR14CONR14R14, —NR14CO2R14, —CO2R14, —NR14R14, —NR14CONR14R14, —C(═NOR14)NR14R14, —CONR14OR14 or —NCOR14, wherein the alkyl, cycloalkyl, alkenyl, alkoxy, aryl, heteroaryl and heterocyclyl may be optionally substituted with one or more R14a's and the heteroaryl and heterocyclyl consist of carbon atoms and 1, 2, 3, or 4 heteroatoms independently selected from the group consisting of N, S, or O;
R13d-1, at each occurrence, is independently H, —OH, F, Cl, Br, I, C1-10 alkyl, C1-10 alkoxy, haloC2-10 alkyl, C3-10 cycloalkyl, C2-12 alkenyl, C2-12 alkynyl, C6-10aryl, a 4- to 12-membered heteroaryl, a 4- to 12-membered heterocyclyl, a 4- to 12-membered heteroaryl-C1-10 alkyl, —CN, —NO2, —NR14SO2R14, ═O, —CONR14R14, —(CH2)m—SO2NR14R14, —(CH2)m—NR14SO2R14, —(CH2)m—NR14SO2NR14R14, —NR14SO2NR14R14, —CO2NR14R14, —NR14CO2NR14R14, —NR14COR14, —SO2NR14COR14, —SO2NR14CONR14R14, —NR14CO2R14, —CO2R14, —NR14CONR14R14, —C(═NOR14)NR14R14, —CONR14OR14 or —NCOR14, wherein the alkyl, cycloalkyl, alkenyl, aryl, heteroaryl and heterocyclyl may be optionally substituted with one or more R14a's and the heteroaryl and heterocyclyl consist of carbon atoms and 1, 2, 3, or 4 heteroatoms independently selected from the group consisting of N, S, or O;
R13d-2, at each occurrence, is independently H, —OH, Cl, Br, I, C1-10 alkyl, C1-10 alkoxy, haloC1-10 alkyl, C3-10 cycloalkyl, C2-12 alkenyl, C2-12 alkynyl, C6-10aryl, a 4- to 12-membered heteroaryl, a 4- to 12-membered heterocyclyl, a 4- to 12-membered heteroaryl-C1-10 alkyl, —CN, —NO2, —(CH2)m—SO2R14, —NR14SO2R14, ═O, —CONR14R14, —(CH2)m—SO2NR14R14, —(CH2)m—NR14SO2R14, —(CH2)m—NR14SO2NR14R14, —NR14SO2NR14R14, —CO2NR14R14, —NR14CO2NR14R14, —NR14COR14, —SO2NR14COR14, —SO2NR14CONR14R14, —NR14CO2R14, —CO2R14, —NR14R14, —NR14CONR14R14, —C(═NOR14)NR14R14, —CONR14OR14 or —NCOR14, wherein the alkyl, cycloalkyl, alkenyl, alkoxy, aryl, heteroaryl and heterocyclyl may be optionally substituted with one or more R14a's and the heteroaryl and heterocyclyl consist of carbon atoms and 1, 2, 3, or 4 heteroatoms independently selected from the group consisting of N, S, or O;
R13d-4, at each occurrence, is independently H, —OH, F, Cl, Br, I, C1-10 alkyl, C1-10 alkoxy, haloC1-10 alkyl, C3-10 cycloalkyl, C2-12 alkenyl, C2-12 alkynyl, C6-10aryl, a 4- to 12-membered heteroaryl, a 4- to 12-membered heterocyclyl, a 4- to 12-membered heteroaryl-C1-10 alkyl, —CN, —NO2, —(CH2)m—SO2R14, —NR14SO2R14, ═O, —CONR14R14, —(CH2)m—SO2NR14R14, —(CH2)m—NR14SO2R14, —(CH2)m—NR14SO2NR14R14, —NR14SO2NR14R14, —CO2NR14R14, —NR14CO2NR14R14, —NR14COR14, —SO2NR14COR14, —SO2NR14CONR14R14, —NR14CO2R14, —CO2R14, —NR14R14, —NR14CONR14R14, —C(═NOR14)NR14R14, —CONR14OR14 or —NCOR14, wherein the alkyl, cycloalkyl, alkenyl, alkoxy, aryl, heteroaryl and heterocyclyl may be optionally substituted with one or more R14a's and the heteroaryl and heterocyclyl consist of carbon atoms and 1, 2, 3, or 4 heteroatoms independently selected from the group consisting of N, S, or O;
R13e, at each occurrence, is independently H, —OH, F, Cl, Br, I, C1-10 alkyl, C1-10 alkoxy, haloC1-10 alkyl, C3-10 cycloalkyl, C2-12 alkenyl, C2-12 alkynyl, C6-10aryl, a 4- to 12-membered heteroaryl, a 4- to 12-membered heterocyclyl, a 4- to 12-membered heteroaryl-C1-10 alkyl, —CN, —NO2, —(CH2)m—SO2R14, ═O, —CONR14R14, —(CH2)m—SO2NR14R14, —(CH2)m—NR14SO2R14, —(CH2).—NR14SO2NR14R14, —NR14SO2NR14R14, —CO2NR14R14, —NR14CO2NR14R14, —NR14COR14, —SO2NR14COR14, —SO2NR14CONR14R14, —NR14CO2R14, —CO2R14, —NR14R14, —NR14CONR14R14, —C(═NOR14)NR14R14, —CONR14OR14 or —NCOR14, wherein the alkyl, cycloalkyl, alkenyl, alkoxy, aryl, heteroaryl and heterocyclyl may be optionally substituted with one or more R14a's and the heteroaryl and heterocyclyl consist of carbon atoms and 1, 2, 3, or 4 heteroatoms independently selected from the group consisting of N, S, or O;
R13ee, at each occurrence, is independently H, —OH, F, Cl, Br, I, C1-10 alkyl, C1-10 alkoxy, haloC1-10 alkyl, C3-10 cycloalkyl, C2-12 alkenyl, C2-12 alkynyl, C6-10aryl, a 4- to 12-membered heteroaryl, a 4- to 12-membered heterocyclyl, a 4- to 12-membered heteroaryl-C1-10 alkyl, —CN, —NO2, —(CH2)m—SO2R14, —NR14SO2R14, —O, —CONR14R14, —(CH2)m—SO2NR14R14, —(CH2)m—NR14SO2R14, —(CH2)m—NR14SO2NR14R14, —NR14SO2NR14R14, —CO2NR14R14, —NR14CO2NR14R14, —NR14COR14, —SO2NR14COR14, —SO2NR14CONR14R14, —NR14CO2R14, —CO2R14, —NR14R14, —NR14CONR14R14, —C(═NOR14)NR14R14, —CONR14OR14 or —NCOR14, wherein the alkyl, cycloalkyl, alkenyl, alkoxy, aryl, heteroaryl and heterocyclyl may be optionally substituted with one or more R14a's and the heteroaryl and heterocyclyl consist of carbon atoms and 1, 2, 3, or 4 heteroatoms independently selected from the group consisting of N, S, or O;
R13e-1, at each occurrence, is independently H, —OH, Cl, Br, I, C1-10 alkyl, C1-10 alkoxy, haloC2-10 alkyl, C3-10 cycloalkyl, C2-12 alkenyl, C2-12 alkynyl, C6-10aryl, a 4- to 12-membered heteroaryl, a 4- to 12-membered heterocyclyl, a 4- to 12-membered heteroaryl-C1-10 alkyl, —CN, —NO2, —(CH2)m—SO2R14, —NR14SO2R14, —O, —(CH2)m—SO2NR14R14, —(CH2)m—NR14SO2R14, —(CH2)m—NR14SO2NR14R14, —NR14SO2NR14R14, —CO2NR14R14, —NR14CO2NR14R14, —SO2NR14COR14, —SO2NR14CONR14R14, —NR14CO2R14, —CO2R14, —NR14R14, —NR14CONR14R14, —C(═NOR14)NR14R14, —CONR14OR14 or —NCOR14, wherein the alkyl, cycloalkyl, alkenyl, alkoxy, aryl, heteroaryl and heterocyclyl may be optionally substituted with one or more R14a's and the heteroaryl and heterocyclyl consist of carbon atoms and 1, 2, 3, or 4 heteroatoms independently selected from the group consisting of N, S, or O;
R13e-2, at each occurrence, is independently H, —OH, F, Cl, Br, I, C1-10 alkyl, C1-10 alkoxy, haloC1-10 alkyl, C3-10 cycloalkyl, C2-12 alkenyl, C2-12 alkynyl, C6-10aryl, a 4- to 12-membered heteroaryl, a 4- to 12-membered heterocyclyl, a 4- to 12-membered heteroaryl-C1-10 alkyl, —CN, —NO2, —(CH2)m—SO2R14, —NR14SO2R14, ═O, —CONR14R14, —(CH2)m—SO2NR14R14, —(CH2)m—NR14SO2R14, —(CH2)m—NR14SO2NR14R14, —NR14SO2NR14R14, —CO2NR14R14, —NR14CO2NR14R14, —NR14COR14, —SO2NR14COR14, —SO2NR14CONR14R14, —NR14CO2R14, —CO2R14, —NR14R14, —NR14CONR14R14, —C(═NOR14)NR14R14, —CONR14OR14 or —NCOR14, wherein the alkyl, cycloalkyl, alkenyl, alkoxy, aryl, heteroaryl and heterocyclyl may be optionally substituted with one or more R14a's and the heteroaryl and heterocyclyl consist of carbon atoms and 1, 2, 3, or 4 heteroatoms independently selected from the group consisting of N, S, or O;
R13f, at each occurrence, is independently H, —OH, F, Cl, Br, I, C1-10 alkyl, C2-10 alkoxy, haloC1-10 alkyl, C3-10 cycloalkyl, C2-12 alkenyl, C2-12 alkynyl, C6-10aryl, a 4- to 12-membered heteroaryl, a 4- to 12-membered heteroaryl-C1-10 alkyl, —CN, —NO2, —(CH2)m—SO2R14, —NR14SO2R14, —CONR14R14, —(CH2)m—SO2NR14R14, —(CH2)m—NR14SO2R14, —(CH2)m—NR14SO2NR14R14, —NR14SO2NR14R14, —CO2NR14R14, —NR14CO2NR14R14, —NR14COR14, —SO2NR14COR14, —SO2NR14CONR14R14, —NR14CO2R14, —CO2R14, —NR14R14, —NR14CONR14R14, —C(═NOR14)NR14R14, —CONR14OR14 or —NCOR14, wherein the alkyl, cycloalkyl, alkenyl, alkoxy, aryl, heteroaryl and heterocyclyl may be optionally substituted with one or more R14a's and the heteroaryl and heterocyclyl consist of carbon atoms and 1, 2, 3, or 4 heteroatoms independently selected from the group consisting of N, S, or O;
R13g, at each occurrence, is independently H, —OH, F, Cl, Br, I, C1-10 alkyl, C1-10 alkoxy, haloC1-10 alkyl, C3-10 cycloalkyl, C2-12 alkenyl, C2-12 alkynyl, C6-10aryl, a 4- to 12-membered heteroaryl, a 4- to 12-membered heterocyclyl, a 4- to 12-membered heteroaryl-C1-10 alkyl, —CN, —NO2, —(CH2)m—SO2R14, —NR14SO2R14, —O, —CONR14R14, —(CH2)m—SO2NR14R14, —(CH2)m—NR14SO2R14, —(CH2)m—NR14SO2NR14R14, —NR14SO2NR14R14, —CO2NR14R14, —NR14CO2NR14R14, —NR14COR14, —SO2NR14COR14, —SO2NR14CONR14R14, —NR14CO2R14, —CO2R14, —NR14R14, —NR14CONR14R14, —C(═NOR14)NR14R14, —CONR14OR14 or —NCOR14, wherein the alkyl, cycloalkyl, alkenyl, alkoxy, aryl, heteroaryl and heterocyclyl may be optionally substituted with one or more R14a's and the heteroaryl and heterocyclyl consist of carbon atoms and 1, 2, 3, or 4 heteroatoms independently selected from the group consisting of N, S, or O;
R13g-2, at each occurrence, is independently H, —OH, F, Cl, Br, I, C2-10 alkyl, C1-10 alkoxy, haloC1-10 alkyl, C3-10 cycloalkyl, C2-12 alkenyl, C2-12 alkynyl, C6-10aryl, a 4- to 12-membered heteroaryl, a 4- to 12-membered heterocyclyl, a 4- to 12-membered heteroaryl-C1-10 alkyl, —CN, —NO2, —(CH2)m—SO2R14, —NR14SO2R14, ═O, —CONR14R14, —(CH2)m—SO2NR14R14, —(CH2)m—NR14SO2R14, —(CH2)m—NR14SO2NR14R14, —NR14SO2NR14R14, —CO2NR14R14, —NR14CO2NR14R14, —NR14COR14, —SO2NR14COR14, —SO2NR14CONR14R14, —NR14CO2R14, —CO2R14, —NR14R14, —NR14CONR14R14, —C(═NOR14)NR14R14, —CONR14OR14 or —NCOR14, wherein the alkyl, cycloalkyl, alkenyl, alkoxy, aryl, heteroaryl and heterocyclyl may be optionally substituted with one or more R14a's and the heteroaryl and heterocyclyl consist of carbon atoms and 1, 2, 3, or 4 heteroatoms independently selected from the group consisting of N, S, or O;
R13h, at each occurrence, is independently H, —OH, F, Cl, Br, I, C1-10 alkyl, C1-10 alkoxy, haloC1-10 alkyl, C3-10 cycloalkyl, C2-12 alkenyl, C2-12 alkynyl, C6-10aryl, a 4- to 12-membered heteroaryl, a 4- to 12-membered heterocyclyl, a 4- to 12-membered heteroaryl-C1-10 alkyl, —CN, —NO2, —(CH2)m—SO2R14, —NR14SO2R14, —O, —CONR14R14, —(CH2)m—SO2NR14R14, —(CH2)m—NR14SO2R14, —(CH2)m—NR14SO2NR14R14, —NR14SO2NR14R14, —CO2NR14R14, —NR14CO2NR14R14, —NR14COR14, —SO2NR14COR14, —SO2NR14CONR14R14, —NR14CO2R14, —CO2R14, —NR14R14, —NR14CONR14R14, —C(═NOR14)NR14R14, —CONR14OR14 or —NCOR14, wherein the alkyl, cycloalkyl, alkenyl, alkoxy, aryl, heteroaryl and heterocyclyl may be optionally substituted with one or more R14a's and the heteroaryl and heterocyclyl consist of carbon atoms and 1, 2, 3, or 4 heteroatoms independently selected from the group consisting of N, S, or O;
R13h-1, at each occurrence, is independently H, —OH, F, Cl, Br, I, C1-10 alkyl, C1-10 alkoxy, haloC1-10 alkyl, C3-10 cycloalkyl, C2-12 alkenyl, C2-12 alkynyl, C7-10aryl, a 4- to 12-membered heteroaryl, a 4- to 12-membered heterocyclyl, a 4- to 12-membered heteroaryl-C1-10 alkyl, —CN, —NO2, —(CH2)m—SO2R14, —NR14SO2R14, ═O, —CONR14R14, —(CH2)m—SO2NR14R14, —(CH2)m—NR14SO2R14, —(CH2)m—NR14SO2NR14R14, —NR14SO2NR14R14, —CO2NR14R14, —NR14CO2NR14R14, —NR14COR14, —SO2NR14COR14, —SO2NR14CONR14R14, —NR14CO2R14, —CO2R14, —NR14R14, —NR14CONR14R14, —C(═NOR14)NR14R14, —CONR14OR14 or —NCOR14, wherein the alkyl, cycloalkyl, alkenyl, alkoxy, aryl, heteroaryl and heterocyclyl may be optionally substituted with one or more R14a's and the heteroaryl and heterocyclyl consist of carbon atoms and 1, 2, 3, or 4 heteroatoms independently selected from the group consisting of N, S, or O;
R13hh, at each occurrence, is independently H, —OH, F, Cl, Br, I, C1-10 alkyl, C1-10 alkoxy, haloC1-10 alkyl, C3-10 cycloalkyl, C2-12 alkenyl, C2-12 alkynyl, C6-10aryl, a 4- to 12-membered heteroaryl, a 4- to 12-membered heterocyclyl, a 4- to 12-membered heteroaryl-C1-10 alkyl, —CN, —NO2, —(CH2)m—SO2R14, —NR14SO2R14, ═O, —CONR14R14, —(CH2)m—SO2NR14R14, —(CH2)m—NR14SO2R14, —(CH2)m—NR14SO2NR14R14, —NR14SO2NR14R14, —CO2NR14R14, —NR14CO2NR14R14, —NR14COR14, —SO2NR14COR14, —SO2NR14CONR14R14, —NR14CO2R14, —CO2R14, —NR14R14, —NR14CONR14R14, —C(═NOR14)NR14R14, —CONR14OR14 or —NCOR14, wherein the alkyl, cycloalkyl, alkenyl, alkoxy, aryl, heteroaryl and heterocyclyl may be optionally substituted with one or more R14a's and the heteroaryl and heterocyclyl consist of carbon atoms and 1, 2, 3, or 4 heteroatoms independently selected from the group consisting of N, S, or O;
R13hh-1, at each occurrence, is independently H, —OH, F, Cl, Br, I, C2-10 alkyl, C1-10 alkoxy, haloC1-10 alkyl, C3-10 cycloalkyl, C2-12 alkenyl, C2-12 alkynyl, C6-10aryl, a 4- to 12-membered heteroaryl, a 4- to 12-membered heterocyclyl, a 4- to 12-membered heteroaryl-C1-10 alkyl, —CN, —NO2, —(CH2)m—SO2R14, —NR14SO2R14, ═O, —CONR14R14, —(CH2)m—SO2NR14R14, —(CH2)m—NR14SO2R14, —(CH2)m—NR14SO2NR14R14, —NR14SO2NR14R14, —CO2NR14R14, —NR14CO2NR14R14, —NR14COR14, —SO2NR14COR14, —SO2NR14CONR14R14, —NR14CO2R14, —CO2R14, —NR14R14, —NR14CONR14R14, —C(═NOR14)NR14R14, —CONR14OR14 or —NCOR14, wherein the alkyl, cycloalkyl, alkenyl, alkoxy, aryl, heteroaryl and heterocyclyl may be optionally substituted with one or more R14a's and the heteroaryl and heterocyclyl consist of carbon atoms and 1, 2, 3, or 4 heteroatoms independently selected from the group consisting of N, S, or O;
R13hh-2, at each occurrence, is independently H, —OH, F, Cl, Br, I, C1-10 alkyl, C1-10 alkoxy, haloC1-10 alkyl, C3-10 cycloalkyl, C2-12 alkenyl, C2-12 alkynyl, C6-10aryl, a 4- to 12-membered heteroaryl, a 4- to 12-membered heterocyclyl, a 4- to 12-membered heteroaryl-C1-10 alkyl, —CN, —NO2, —(CH2)m—SO2R14, —NR14SO2R14, —O, —CONR14R14, —(CH2)m—SO2NR14R14, —(CH2)m—NR14SO2R14, —(CH2)m—NR14SO2NR14R14, —NR14SO2NR14R14, —CO2NR14R14, —NR14CO2NR14R14, —NR14COR14, —SO2NR14COR14, —SO2NR14CONR14R14, —NR14CO2R14, —CO2R14, —NR14R14, —NR14CONR14R14, —C(═NOR14)NR14R14, —CONR14OR14 or —NCOR14, wherein the alkyl, cycloalkyl, alkenyl, alkoxy, aryl, heteroaryl and heterocyclyl may be optionally substituted with one or more R14a's and the heteroaryl and heterocyclyl consist of carbon atoms and 1, 2, 3, or 4 heteroatoms independently selected from the group consisting of N, S, or O;
R13j, at each occurrence, is independently H, —OH, F, Cl, Br, I, C1-10 alkyl, C1-10 alkoxy, haloC1-10 alkyl, C3-10 cycloalkyl, C2-12 alkenyl, C2-12 alkynyl, C6-10aryl, a 4- to 12-membered heteroaryl, a 4- to 12-membered heterocyclyl, a 4- to 12-membered heteroaryl-C1-10 alkyl, —CN, —NO2, —(CH2)m—SO2R14, ═O, —CONR14R14, —(CH2)m—SO2NR14R14, —(CH2)m—NR14SO2R14, —(CH2)m—NR14SO2NR14R14, —NR14SO2NR14R14, —CO2NR14R14, —NR14CO2NR14R14, —NR14COR14, —SO2NR14COR14, —SO2NR14CONR14R14, —NR14CO2R14, —CO2R14, —NR14R14, —NR14CONR14R14, —C(═NOR14)NR14R14, —CONR14OR14 or —NCOR14, wherein the alkyl, cycloalkyl, alkenyl, alkoxy, aryl, heteroaryl and heterocyclyl may be optionally substituted with one or more R14a's and the heteroaryl and heterocyclyl consist of carbon atoms and 1, 2, 3, or 4 heteroatoms independently selected from the group consisting of N, S, or O;
R13m, at each occurrence, is independently H, —OH, F, Cl, Br, I, C1-10 alkyl, C1-10 alkoxy, haloC1-10 alkyl, C3-10 cycloalkyl, C2-12 alkenyl, C2-12 alkynyl, C6-10aryl, a 4- to 12-membered heteroaryl, a 4- to 12-membered heterocyclyl, a 4- to 12-membered heteroaryl-C1-10 alkyl, —CN, —NO2, —(CH2)m—SO2R14, —NR14SO2R14, —O, —CONR14R14, —(CH2)m—SO2NR14R14, —(CH2)m—NR14SO2R14, —(CH2)m—NR14SO2NR14R14, —NR14SO2NR14R14, —CO2NR14R14, —NR14CO2NR14R14, —NR14COR14, —SO2NR14COR14, —SO2NR14CONR14R14, —NR14CO2R14, —CO2R14, —NR14R14, —NR14CONR14R14, —C(═NOR14)NR14R14, —CONR14OR14 or —NCOR14, wherein the alkyl, cycloalkyl, alkenyl, alkoxy, aryl, heteroaryl and heterocyclyl may be optionally substituted with one or more R14a's and the heteroaryl and heterocyclyl consist of carbon atoms and 1, 2, 3, or 4 heteroatoms independently selected from the group consisting of N, S, or O;
R13m-1, at each occurrence, is independently H, —OH, F, Cl, Br, I, C1-10 alkyl, C1-10 alkoxy, haloC1-10 alkyl, C3-10 cycloalkyl, C2-12 alkenyl, C2-12 alkynyl, C6-10aryl, a 4- to 12-membered heteroaryl, a 4- to 12-membered heterocyclyl, a 4- to 12-membered heteroaryl-C1-10 alkyl, —CN, —NO2, —(CH2)m—SO2R14, —NR14SO2R14, ═O, —CONR14R14, —(CH2)m—SO2NR14R14, —(CH2)m—NR14SO2R14, —(CH2)m—NR14SO2NR14R14, —NR14SO2NR14R14, —CO2NR14R14, —NR14CO2NR14R14, —NR14COR14, —SO2NR14COR14, —SO2NR14CONR14R14, —NR14CO2R14, —CO2R14, —NR14R14, —NR14CONR14R14, —C(═NOR14)NR14R14, —CONR14OR14 or —NCOR14, wherein the alkyl, cycloalkyl, alkenyl, alkoxy, aryl, heteroaryl and heterocyclyl may be optionally substituted with one or more R14a's and the heteroaryl and heterocyclyl consist of carbon atoms and 1, 2, 3, or 4 heteroatoms independently selected from the group consisting of N, S, or O;
R13n-1, at each occurrence, is independently H, —OH, F, Cl, Br, I, C2-10 alkyl, C1-10 alkoxy, haloC1-10 alkyl, C3-10 cycloalkyl, C2-12 alkenyl, C2-12 alkynyl, C6-10aryl, a 4- to 12-membered heteroaryl, a 4- to 12-membered heterocyclyl, a 4- to 12-membered heteroaryl-C1-10 alkyl, —CN, —NO2, —(CH2)m—SO2R14, —NR14SO2R14, ═O, —CONR14R14, —(CH2)m—SO2NR14R14, —(CH2)m—NR14SO2R14, —(CH2)m—NR14SO2NR14R14, —NR14SO2NR14R14, —CO2NR14R14, —NR14CO2NR14R14, —NR14COR14, —SO2NR14COR14, —SO2NR14CONR14R14, —NR14CO2R14, —CO2R14, —NR14R14, —NR14CONR14R14, —C(═NOR14)NR14R14, —CONR14OR14 or —NCOR14, wherein the alkyl, cycloalkyl, alkenyl, alkoxy, aryl, heteroaryl and heterocyclyl may be optionally substituted with one or more R14a's and the heteroaryl and heterocyclyl consist of carbon atoms and 1, 2, 3, or 4 heteroatoms independently selected from the group consisting of N, S, or O;
R13p, at each occurrence, is independently H, —OH, F, Cl, Br, I, C1-10 alkyl, C1-10 alkoxy, haloC1-10 alkyl, C3-10 cycloalkyl, C2-12 alkenyl, C2-12 alkynyl, C6-10aryl, a 4- to 12-membered heteroaryl, a 4- to 12-membered heterocyclyl, a 4- to 12-membered heteroaryl-C1-10 alkyl, —CN, —NO2, —(CH2)m—SO2R14, —NR14SO2R14, ═O, —CONR14R14, —(CH2)m—SO2NR14R14, —(CH2)m NR14SO2R14, —(CH2)m—NR14SO2NR14R14, —NR14SO2NR14R14, —CO2NR14R14, —NR14CO2NR14R14, —NR14COR14, —SO2NR14COR14, —SO2NR14CONR14R14, —NR14CO2R14, —CO2R14, —NR14R14, —NR14CONR14R14, —C(═NOR14)NR14R14, —CONR14OR14 or —NCOR14, wherein the alkyl, cycloalkyl, alkenyl, alkoxy, aryl, heteroaryl and heterocyclyl may be optionally substituted with one or more R14a's and the heteroaryl and heterocyclyl consist of carbon atoms and 1, 2, 3, or 4 heteroatoms independently selected from the group consisting of N, S, or O;
R13p-1, at each occurrence, is independently H, —OH, F, Cl, Br, I, C1-10 alkyl, C1-10 alkoxy, haloC1-10 alkyl, C3-10 cycloalkyl, C2-12 alkenyl, C2-12 alkynyl, C6-10aryl, a 4- to 12-membered heteroaryl, a 4- to 12-membered heterocyclyl, a 4- to 12-membered heteroaryl-C1-10 alkyl, —CN, —NO2, —(CH2)m—SO2R14, —NR14SO2R14, —O, —CONR14R14, —(CH2)m—SO2NR14R14, —(CH2)m—NR14SO2R14, —(CH2)m—NR14SO2NR14R14, —NR14SO2NR14R14, —CO2NR14R14, —NR14CO2NR14R14, —NR14COR14, —SO2NR14COR14, —SO2NR14CONR14R14, —NR14CO2R14, —CO2R14, —NR14R14, —NR14CONR14R14, —C(═NOR14)NR14R14, —CONR14OR14 or —NCOR14, wherein the alkyl, cycloalkyl, alkenyl, alkoxy, aryl, heteroaryl and heterocyclyl may be optionally substituted with one or more R14a's and the heteroaryl and heterocyclyl consist of carbon atoms and 1, 2, 3, or 4 heteroatoms independently selected from the group consisting of N, S, or O;
R13p-2, at each occurrence, is independently H, —OH, F, Cl, Br, I, C1-10 alkyl, C1-10 alkoxy, haloC1-10 alkyl, C3-10 cycloalkyl, C2-12 alkenyl, C2-12 alkynyl, C6-10aryl, a 4- to 12-membered heteroaryl, a 4- to 12-membered heterocyclyl, a 4- to 12-membered heteroaryl-C1-10 alkyl, —CN, —NO2, —(CH2)m—SO2R14, —NR14SO2R14, ═O, —CONR14R14, —(CH2)m—SO2NR14R14, —(CH2)m—NR14SO2R14, —(CH2)m—NR14SO2NR14R14, —NR14SO2NR14R14, —CO2NR14R14, —NR14CO2NR14R14, —NR14COR14, —SO2NR14COR14, —SO2NR14CONR14R14, —NR14CO2R14, —CO2R14, —NR14R14, —NR14CONR14R14, —C(═NOR14)NR14R14, —CONR14OR14 or —NCOR14, wherein the alkyl, cycloalkyl, alkenyl, alkoxy, aryl, heteroaryl and heterocyclyl may be optionally substituted with one or more R14a's and the heteroaryl and heterocyclyl consist of carbon atoms and 1, 2, 3, or 4 heteroatoms independently selected from the group consisting of N, S, or O;
R13q, at each occurrence, is independently H, —OH, F, Cl, Br, I, C2-10 alkyl, C1-10 alkoxy, haloC2-10 alkyl, C3-10 cycloalkyl, C2-12 alkenyl, C2-12 alkynyl, C6-10aryl, a 4- to 12-membered heteroaryl, a 4- to 12-membered heterocyclyl, a 4- to 12-membered heteroaryl-C1-10 alkyl, —CN, —NO2, —(CH2)m—SO2R14, —NR14SO2R14, ═O, —CONR14R14, —(CH2)m—SO2NR14R14, —(CH2)m—NR14SO2R14, —(CH2)m—NR14SO2NR14R14, —NR14SO2NR14R14, —CO2NR14R14, —NR14CO2NR14R14, —NR14COR14, —SO2NR14COR14, —SO2NR14CONR14R14, —NR14CO2R14, —CO2R14, —NR14R14, —NR14CONR14R14, —C(═NOR14)NR14R14, —CONR14OR14 or —NCOR14, wherein the alkyl, cycloalkyl, alkenyl, alkoxy, aryl, heteroaryl and heterocyclyl may be optionally substituted with one or more R14a's and the heteroaryl and heterocyclyl consist of carbon atoms and 1, 2, 3, or 4 heteroatoms independently selected from the group consisting of N, S, or O;
R13q-1, at each occurrence, is independently H, —OH, F, Cl, Br, I, C1-10 alkyl, C1-10 alkoxy, haloC1-10 alkyl, C3-10 cycloalkyl, C2-12 alkenyl, C2-12 alkynyl, C6-10aryl, a 4- to 12-membered heteroaryl, a 4- to 12-membered heterocyclyl, a 4- to 12-membered heteroaryl-C1-10 alkyl, —CN, —NO2, —(CH2)m—SO2R14, —NR14SO2R14, ═O, —CONR14R14, —(CH2)m—SO2NR14R14, —(CH2)m—NR14SO2R14, —(CH2)m—NR14SO2NR14R14, —NR14SO2NR14R14, —CO2NR14R14, —NR14CO2NR14R14, —NR14COR14, —SO2NR14COR14, —SO2NR14CONR14R14, —NR14CO2R14, —CO2R14, —NR14R14, —NR14CONR14R14, —C(═NOR14)NR14R14, —CONR14OR14 or —NCOR14, wherein the alkyl, cycloalkyl, alkenyl, alkoxy, aryl, heteroaryl and heterocyclyl may be optionally substituted with one or more R14a's and the heteroaryl and heterocyclyl consist of carbon atoms and 1, 2, 3, or 4 heteroatoms independently selected from the group consisting of N, S, or O;
R13q-2, at each occurrence, is independently H, —OH, F, Cl, Br, I, C1-10 alkyl, C1-10 alkoxy, haloC1-10 alkyl, C3-10 cycloalkyl, C2-12 alkenyl, C2-12 alkynyl, C6-10aryl, a 4- to 12-membered heteroaryl, a 4- to 12-membered heterocyclyl, a 4- to 12-membered heteroaryl-C1-10 alkyl, —CN, —NO2, —(CH2)m—SO2R14, —NR14SO2R14, —CONR14R14, —(CH2)m—SO2NR14R14, —(CH2)m—NR14SO2R14, —(CH2)m—NR14SO2NR14R14, —NR14SO2NR14R14, —CO2NR14R14, —NR14CO2NR14R14, —NR14COR14, —SO2NR14COR14, —SO2NR14CONR14R14, —NR14CO2R14, —CO2R14, —NR14R14, —NR14CONR14R14, —C(═NOR14)NR14R14, —CONR14OR14 or —NCOR14, wherein the alkyl, cycloalkyl, alkenyl, alkoxy, aryl, heteroaryl and heterocyclyl may be optionally substituted with one or more R14a's and the heteroaryl and heterocyclyl consist of carbon atoms and 1, 2, 3, or 4 heteroatoms independently selected from the group consisting of N, S, or O;
R14, at each occurrence, is independently selected from hydrogen, C1-10 alkyl, C3-10 cycloalkyl, C6-10 aryl, a 4- to 12-membered heteroaryl or a 4- to 12-membered heterocyclyl, wherein the alkyl, cycloalkyl, aryl, heteroaryl and heterocyclyl may be optionally substituted with be optionally substituted with 0-3 R14a and the heteroaryl and heterocyclyl consist of carbon atoms and 1, 2, 3, or 4 heteroatoms independently selected from the group consisting of N, S, or O;
or
two R14's are taken together with the atoms to which they are attached to form a cyclic ring, wherein the cyclic ring may be optionally substituted with one or more R24a's and optionally contain 1, 2, 3, or 4 heteroatoms independently selected from the group consisting of N, S, or O;
R14a, at each occurrence, is independently selected from F, Cl, Br, I, C1-10 alkyl, haloC1-10alkyl, C6-10aryl, C3-10cycloalkyl, a 4- to 12-membered heteroaryl, a 4- to 12-membered heterocyclyl, F, Cl, Br, I, —CN, —NO2, —CO2R26, —CO2NR24R24, —OCF3, —OR25, —O, —CONR24R24, —COR24, —SO2R24, —NR24R24, —NR24CO2R24, —SO2NR24R24, or C6-10 arylC1-10 alkyl, wherein the heteroaryl and heterocyclyl consist of carbon atoms and 1, 2, 3, or 4 heteroatoms independently selected from the group consisting of N, S, or O;
R24, at each occurrence, is independently selected from hydrogen, C1-10alkyl, C3-10cycloalkyl, C6-10aryl, a 4- to 12-membered heteroaryl or 4- to 12-membered heterocyclyl, wherein the alkyl, aryl, heteroaryl and heterocyclyl may be optionally substituted with one or more R24a's and the heteroaryl and heterocyclyl consist of carbon atoms and 1, 2, 3, or 4 heteroatoms independently selected from the group consisting of N, S, or O;
or
two R24's are taken together with the atoms to which they are attached to form a cyclic ring, wherein the cyclic ring may be optionally substituted with one or more R24a's and optionally contain 1, 2, 3, or 4 heteroatoms independently selected from the group consisting of N, S, or O;
R24a, at each occurrence, is independently selected from F, Cl, Br, I, C1-10 alkyl, haloC1-10alkyl, C6-10aryl, C3-10cycloalkyl, a 4- to 12-membered heteroaryl, a 4- to 12-membered heterocyclyl, —CN, —NO2, —CO2R25, —OCF3, —OR25, ═O, —CONR25R25, —COR25, —NR25R25, —NR25CO2R25, or C6-10arylC1-10alkyl, wherein the heteroaryl and heterocyclyl consist of carbon atoms and 1, 2, 3, or 4 heteroatoms independently selected from the group consisting of N, S, or O;
R24b, at each occurrence, is independently selected from C1-10 alkyl, C6-10aryl, C3-10cycloalkyl, a 4- to 12-membered heteroaryl, a 4- to 12-membered heterocyclyl, —CO2R25, —SO2NR25R25, —COR25 or C6-10arylC1-10alkyl, wherein the heteroaryl and heterocyclyl consist of carbon atoms and 1, 2, 3, or 4 heteroatoms independently selected from the group consisting of N, S, or O;
R25, at each occurrence, is independently selected from hydrogen, C1-10alkyl, C3-10cycloalkyl, C6-10aryl, a 4- to 12-membered heteroaryl or 4- to 12-membered heterocyclyl, wherein the heteroaryl and heterocyclyl consist of carbon atoms and 1, 2, 3, or 4 heteroatoms independently selected from the group consisting of N, S, or O;
and
R26, at each occurrence, is independently selected from C1-10alkyl, haloC1-10alkyl, C3-10cycloalkyl, C6-10aryl, a 4- to 12-membered heteroaryl or 4- to 12-membered heterocyclyl, wherein the heteroaryl and heterocyclyl consist of carbon atoms and 1, 2, 3, or 4 heteroatoms independently selected from the group consisting of N, S, or O;
provide that:
(i) R1 is not Cl when m is 0, 1 or 2;
R13a-1 is H, —CF3, or methoxy;
R13c-1 is H, OH, methoxy or dimethylamino;
X, Y, Z, R13b-1, R13d-1, R13a-2, R13b-2, R13c-2, R13d-2, R13e-2, R13g-2, R13a-4, R13b-4, R13c-4, R13d-4, R13b-5, R13c-5, R13m-1, R13n-1, R13p-1, and R13q-1 are H;
and
(ii) m is not 0 or 1 when X, Y, R13a, R13d, R13e, R13g, R13a-2, R13b-2, R13c-2, R13d-2, R13a-4, R13b-4, R13c-4, R13d-4 R13b-5, R13c-5, R13h-1 and R13hh-1 are H;
R13b is H or —SO2NH2;
R13c is H, —CONH2, —SO2N(C2H4OH)2, —SO2NHCOCH3, —SO2NH2, -tetrazolyl or (4-aminopiperidinyl)sulfonyl;
R13f is H or —NHC2H4OCH3;
and Z is H, —CO2H, or —CO2CH3.

92 more elements

Facts

Application

13/393,328Filed 1 Sep 2010

Priority

3 Sep 2009

Published

13 Sep 2012

Term ends

Not estimatedThe source records don’t support an estimate.

Classification29 codes

C07D 401/14
Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a…:…
A61K 31/517
Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim: ortho- or peri-condensed with carbocyclic ring systems, e.g. quinazoline, perimidine
A61K 31/5377
1,4-Oxazines, e.g. morpholine: not condensed and containing further heterocyclic rings, e.g. timolol
A61K 31/549
Having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame: having two or more nitrogen atoms in…